86604-75-3

Basic information

• Product Name: 2-Chloromethyl-4-methoxy-3,5-dimethylpyridine hydrochloride
• Synonyms: 2-CHLOROMETHYL-3,5-DIMETHYL-4-METHOXYPYRIDINE HCL;2-CHLOROMETHYL-3,5-DIMETHYL-4-METHOXYPYRIDINE HYDROCHLORIDE;2-CHLOROMETHYL-4-METHOXY-3,5-DIMETHYL PYRIDINE HCL;2-(CHLOROMETHYL)-4-METHOXY-3,5-DIMETHYLPYRIDINE HYDROCHLORIDE;2-(CHLOROMETHYL)-4-METHOXY-3,5-LUTIDINE HCL;2-CHLOROMETHYL-4-METHOXY-3,5-LUTIDINE HYDROCHLORIDE;CMDM;Omeprazole intermediate
• CAS NO: 86604-75-3
• Molecular Formula: C₉H₁₂ClNO*ClH
• Molecular Weight: 222.11
• EINECS: -0
• Product Categories: C9 to C46Heterocyclic Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Pyridines;Aromatics;Heterocycles;Intermediates;OLED materials,pharm chemical,electronic;Heterocycle-Pyridine series
• Mol File: 86604-75-3.mol
• Article Data: 17

Chemical Properties

• Melting Point: 128-131 °C(lit.)
• Boiling Point: 272.2 °C at 760 mmHg
• Flash Point: 118.4 °C
• Appearance: /
• Storage Temp.: Refrigerator, Under Inert Atmosphere
• Solubility: Chloroform (Slightly), Methanol (Sparingly)
• Water Solubility: Soluble in water.
• CAS DataBase Reference: 2-Chloromethyl-4-methoxy-3,5-dimethylpyridine hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloromethyl-4-methoxy-3,5-dimethylpyridine hydrochloride(86604-75-3)
• EPA Substance Registry System: 2-Chloromethyl-4-methoxy-3,5-dimethylpyridine hydrochloride(86604-75-3)

Safety Data

• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: 3261
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 86604-75-3(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

2-Chloromethyl-4-methoxy-3,5-dimethylpyridine hydrochloride is used as pharmaceutical intermediates. It is an intermediate in the production of the antiulcer agent Omeprazole.

Synthetic route

(4-methoxy-3,5-dimethylpyridin-2-yl)methanol (86604-78-6) → 2-(chloromethyl)-4-methoxy-3,5-dimethylpyridine hydrochloride (86604-75-3)

Conditions	Yield
With thionyl chloride In dichloromethane at 20℃; for 1h;	100%
With thionyl chloride In dichloromethane at 20℃; for 1h;	100%
With bis(trichloromethyl) carbonate; Triphenylphosphine oxide In toluene at 20 - 60℃; for 6h; Temperature;	98%

(chloromethyl)-4-methoxy-3,5-dimethylpyridine (84006-10-0) → 2-(chloromethyl)-4-methoxy-3,5-dimethylpyridine hydrochloride (86604-75-3)

Conditions	Yield
With hydrogenchloride In toluene at 15℃; for 0.1h;	94.5%
With hydrogenchloride In ethanol at 20℃; for 1h; Inert atmosphere;	92.6%

2,3,5-trimethyl-pyridine (695-98-7) → 2-(chloromethyl)-4-methoxy-3,5-dimethylpyridine hydrochloride (86604-75-3)

Conditions	Yield
Multi-step reaction with 6 steps 1: 76 percent / 30percent aq. H2O2, HOAc / 23 h / 90 °C 2: HNO3 / Heating 4: 110 °C 5: aq. NaOH / methanol / Heating 6: 90 percent / SOCl2 / CH2Cl2 / 0.5 h / Heating View Scheme

2,3,5-trimethyl-4-nitropyridine N-oxide (86604-79-7) → 2-(chloromethyl)-4-methoxy-3,5-dimethylpyridine hydrochloride (86604-75-3)

Conditions	Yield
Multi-step reaction with 4 steps 2: 110 °C 3: aq. NaOH / methanol / Heating 4: 90 percent / SOCl2 / CH2Cl2 / 0.5 h / Heating View Scheme
Multi-step reaction with 4 steps 1: NaOMe / 16 h / 40 °C 2: 2 h / 90 °C 3: 2 N aq. NaOH / 2 h / 80 °C 4: SOCl2 / CH2Cl2 / 2 h / 0 - 5 °C View Scheme

2,3,5-trimethylpyridine 1-oxide (74409-42-0) → 2-(chloromethyl)-4-methoxy-3,5-dimethylpyridine hydrochloride (86604-75-3)

Conditions	Yield
Multi-step reaction with 5 steps 1: HNO3 / Heating 3: 110 °C 4: aq. NaOH / methanol / Heating 5: 90 percent / SOCl2 / CH2Cl2 / 0.5 h / Heating View Scheme
Multi-step reaction with 5 steps 1: 98percent HNO3 / acetic acid / 33 h / 80 °C 2: NaOMe / 16 h / 40 °C 3: 2 h / 90 °C 4: 2 N aq. NaOH / 2 h / 80 °C 5: SOCl2 / CH2Cl2 / 2 h / 0 - 5 °C View Scheme

4-methoxy-2,3,5-trimethylpyridine 1-oxide (86604-80-0) → 2-(chloromethyl)-4-methoxy-3,5-dimethylpyridine hydrochloride (86604-75-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: 110 °C 2: aq. NaOH / methanol / Heating 3: 90 percent / SOCl2 / CH2Cl2 / 0.5 h / Heating View Scheme
Multi-step reaction with 3 steps 1: 2 h / 90 °C 2: 2 N aq. NaOH / 2 h / 80 °C 3: SOCl2 / CH2Cl2 / 2 h / 0 - 5 °C View Scheme
Multi-step reaction with 3 steps 1: acetic acid / methanol; toluene 2: sodium hydroxide / methanol 3: thionyl chloride View Scheme
Multi-step reaction with 3 steps 1: Raney nickel / methanol / 6 h / 40 °C 2: trichloroisocyanuric acid / chloroform / 4 h / 50 °C 3: hydrogenchloride / toluene / 0.1 h / 15 °C View Scheme

(4-methoxy-3,5-dimethyl-pyridin-2-yl)methyl acetate (91219-90-8) → 2-(chloromethyl)-4-methoxy-3,5-dimethylpyridine hydrochloride (86604-75-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: aq. NaOH / methanol / Heating 2: 90 percent / SOCl2 / CH2Cl2 / 0.5 h / Heating View Scheme
Multi-step reaction with 2 steps 1: 2 N aq. NaOH / 2 h / 80 °C 2: SOCl2 / CH2Cl2 / 2 h / 0 - 5 °C View Scheme
Multi-step reaction with 2 steps 1: sodium hydroxide / methanol 2: thionyl chloride View Scheme

SO2 Cl2 + (4-methoxy-3,5-dimethylpyridin-2-yl)methanol (86604-78-6) → 2-chloromethyl-5-dimethyl-4-methoxypyridine hydrochloride + 2-(chloromethyl)-4-methoxy-3,5-dimethylpyridine hydrochloride (86604-75-3)

Conditions	Yield
In chloroform

isopropyl alcohol (67-63-0) + 3,5-dimethyl-4-methoxy-2-cyanopyridine (104916-41-8) → 2-(chloromethyl)-4-methoxy-3,5-dimethylpyridine hydrochloride (86604-75-3)

Conditions	Yield
With sodium hydroxide; thionyl chloride; sodium nitrite; aluminum nickel In NH3 -saturated methanol; water; acetic acid

2-Hydroxymethyl-4-methoxy-3,5-dimethylpyridine hydrochloride (96300-88-8) → 2-(chloromethyl)-4-methoxy-3,5-dimethylpyridine hydrochloride (86604-75-3)

Conditions	Yield
With thionyl chloride In dichloromethane at 15 - 30℃; for 1h;
With thionyl chloride

4-chloro-2,3,5-trimethylpyridine 1-oxide (109371-20-2) → 2-(chloromethyl)-4-methoxy-3,5-dimethylpyridine hydrochloride (86604-75-3)

Conditions	Yield
Multi-step reaction with 4 steps 1: sodium hydroxide 2: acetic acid / methanol; toluene 3: sodium hydroxide / methanol 4: thionyl chloride View Scheme

3-[4-(2-mercapto-5-methoxy-benzimidazole-1-sulfonyl)-phenyl]-propionic acid 2-(toluene-4-sulfonyl)ethyl ester (651729-89-4) + 2-(chloromethyl)-4-methoxy-3,5-dimethylpyridine hydrochloride (86604-75-3) → 3-[4-(5-methoxy-2-(4-methoxy-3,5-dimethyl-pyridin-2-ylmethylsulfanyl)benzimidazole-1-sulfonyl)-phenyl]-propionic acid 2-(toluene-4-sulfonyl)ethyl ester (651729-90-7)

Conditions	Yield
With potassium carbonate In DMF (N,N-dimethyl-formamide) for 2h;	100%
With potassium carbonate In DMF (N,N-dimethyl-formamide) for 2h;	100%

N-{5-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-yl}-acetamide (848694-70-2) + 2-(chloromethyl)-4-methoxy-3,5-dimethylpyridine hydrochloride (86604-75-3) → N-[5-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-chloro-7-(4-methoxy-3,5-dimethyl-pyridin-2-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidin-2-yl]-acetamide (848694-71-3)

Conditions	Yield
With potassium carbonate In DMF (N,N-dimethyl-formamide) at 20℃;	100%

2-Mercapto-5-methoxybenzimidazole (37052-78-1) + 2-(chloromethyl)-4-methoxy-3,5-dimethylpyridine hydrochloride (86604-75-3) → omeprazole sulfide (73590-85-9)

Conditions	Yield
With tetrabutylammomium bromide; edetate disodium; sodium hydroxide In dichloromethane; water pH=10; pH-value;	100%
With sodium hydroxide at 20℃;	98%
With sodium hydroxide In methanol; water Reflux;	95.2%

phthalimide (136918-14-4) + 2-(chloromethyl)-4-methoxy-3,5-dimethylpyridine hydrochloride (86604-75-3) → 2-((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)isoindoline-1,3-dione (946071-49-4)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 16h;	100%

2-(chloromethyl)-4-methoxy-3,5-dimethylpyridine hydrochloride (86604-75-3) + 5-methoxy-1H-imidazo[4,5-b]pyridine-2-thiol → 5-methoxy-2-((4-methoxy-3,5-dimethylpyridin-2-yl)methylthio)-1H-imidazo[4,5-b]pyridine (113713-24-9)

Conditions	Yield
With sodium hydroxide In water at 25 - 30℃; Large scale reaction;	98%
With sodium hydroxide In methanol; water at 25 - 30℃; for 0.75h;	88.8%

tert-butyl 4-(6-Hydroxy-2-methylpyridin-3-yl)piperidine-1-carboxylate + 2-(chloromethyl)-4-methoxy-3,5-dimethylpyridine hydrochloride (86604-75-3) → tert-butyl 4-{6-[(4-methoxy-3,5-dimethylpyridin-2-yl)-methoxy]-2-methylpyridin-3-yl}piperidine-1-carboxylate

Conditions	Yield
With silver carbonate In toluene at 110℃; for 6h; Darkness;	98%

2-(chloromethyl)-4-methoxy-3,5-dimethylpyridine hydrochloride (86604-75-3) + 5-tert-butyl-2-mercapto-1H-benzimidazole (92806-76-3) → 5-tert-Butyl-2-(4-methoxy-3,5-dimethyl-pyridin-2-ylmethylsulfanyl)-1H-benzoimidazole

Conditions	Yield
With sodium hydroxide In methanol Heating;	97%

2-(chloromethyl)-4-methoxy-3,5-dimethylpyridine hydrochloride (86604-75-3) + N,N`-dimethylethylenediamine (110-70-3) → N,N′‑dimethyl‑N,N′‑bis(4‑methoxy‑3,5‑dimethylpyridine‑2‑ylmethyl)‑1,2 diaminoethane (1523156-35-5)

Conditions	Yield
Stage #1: 2-(chloromethyl)-4-methoxy-3,5-dimethylpyridine hydrochloride With potassium carbonate In water at 20℃; for 0.5h; Stage #2: N,N`-dimethylethylenediamine With sodium hydroxide In dichloromethane; water at 20℃; for 60h;	97%
With sodium hydroxide In dichloromethane; water

2-Mercapto-5-methoxybenzimidazole (37052-78-1) + 2-(chloromethyl)-4-methoxy-3,5-dimethylpyridine hydrochloride (86604-75-3) → 6-methoxy-2-(((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)thio)-1H-benzo[d]imidazole (73590-85-9)

Conditions	Yield
With sodium hydroxide In 1,4-dioxane; water at 80℃; for 1h; Solvent; Temperature;	97%
With sodium hydroxide In methanol; water at 55 - 65℃; for 2h; Large scale;	86%
With sodium hydrogencarbonate In ethanol Reagent/catalyst; Temperature; Solvent; Reflux; Large scale;	85.3%
With sodium hydroxide In ethanol; water Solvent; Reflux; Large scale;	81.1%
With sodium hydroxide In methanol at 50℃; for 4h; Reagent/catalyst; Temperature; Solvent;	34.1 g

4-(2-mercapto-5-methoxy-benzimidazole-1-sulfonyl)-3-methoxy-benzoic acid 2-(toluene-4-sulfonyl)ethyl ester (843615-24-7) + 2-(chloromethyl)-4-methoxy-3,5-dimethylpyridine hydrochloride (86604-75-3) → 4-methoxy-3-[5-methoxy-2-(4-methoxy-3,5-dimethyl-pyridin-2-ylmethylsulfanyl)-benzimidazole-1-sulfonyl]-benzoic acid 2-(toluene-4-sulfonyl)ethyl ester (651729-67-8)

Conditions	Yield
With potassium carbonate In DMF (N,N-dimethyl-formamide) for 2h;	96%
With potassium carbonate In DMF (N,N-dimethyl-formamide) for 2h;	96%

2-(chloromethyl)-4-methoxy-3,5-dimethylpyridine hydrochloride (86604-75-3) + 6-methoxy-1H-benzoimidazole-2-thiol (37052-78-1) → omeprazole (73590-58-6)

Conditions	Yield
Stage #1: 6-methoxy-1H-benzoimidazole-2-thiol With sodium hydroxide In ethanol; water at 70 - 90℃; Stage #2: 2-(chloromethyl)-4-methoxy-3,5-dimethylpyridine hydrochloride With hydrogenchloride In ethanol; water at -10 - 30℃; for 4h; Reflux;	96%

1-(p-toluenesulfonyl)-1,4,7-triazacyclononane (129422-96-4) + 2-(chloromethyl)-4-methoxy-3,5-dimethylpyridine hydrochloride (86604-75-3) → C31H43N5O4S

Conditions	Yield
With tetrabutylammomium bromide; sodium carbonate In acetonitrile for 24h; Inert atmosphere; Reflux;	96%
With tetrabutylammomium bromide; sodium carbonate In acetonitrile for 22h; Reflux; Inert atmosphere;	91%

5-methoxy-1,3-dihydro-2H-benzo[d]imidazole-2-thione (37052-78-1) + 2-(chloromethyl)-4-methoxy-3,5-dimethylpyridine hydrochloride (86604-75-3) → omeprazole sulfide (73590-85-9)

Conditions	Yield
With sodium carbonate In methanol for 1.5h; Reflux;	95%
In methanol at 70℃; Kinetics;

tert-butyl (3-(methoxymethoxy)phenyl)carbamate (136247-90-0) + 2-(chloromethyl)-4-methoxy-3,5-dimethylpyridine hydrochloride (86604-75-3) → tert-butyl ((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)(3-(methoxymethoxy)phenyl)carbamate

Conditions	Yield
Stage #1: tert-butyl (3-(methoxymethoxy)phenyl)carbamate With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 0.5h; Stage #2: 2-(chloromethyl)-4-methoxy-3,5-dimethylpyridine hydrochloride In N,N-dimethyl-formamide at 0 - 20℃; for 12h;	95%

5-(difluoromethoxy)-2-mercapto-1H-benzimidazole (97963-62-7) + 2-(chloromethyl)-4-methoxy-3,5-dimethylpyridine hydrochloride (86604-75-3) → pantoprazole sulfide (102625-64-9)

Conditions	Yield
With sodium hydroxide In ethanol at 80℃; for 8h;	94%

2-(chloromethyl)-4-methoxy-3,5-dimethylpyridine hydrochloride (86604-75-3) + 2-hydroxy-4-methyl-5-bromopyridine (164513-38-6) → 2-{[(5-bromo-4-methylpyridin-2-yl)oxy]methyl}-4-methoxy-3,5-dimethylpyridine

Conditions	Yield
With silver carbonate In toluene at 110℃; for 6h; Darkness;	94%

2-(4-tolylsulfonyl)ethyl 3-{4-[2-mercapto-5-methoxybenzimidazolyl]sulfonyl}-3,5-dimethylphenoxy-2,2-dimethylpropionate + 2-(chloromethyl)-4-methoxy-3,5-dimethylpyridine hydrochloride (86604-75-3) → 2-(4-tolylsulfonyl)ethyl 3-{4-[(5-methoxy-2-{[4-methoxy-3,5-dimethyl(2-pyridyl)]methylthio}benzimidazolyl)sulfonyl]-3,5-dimethylphenoxy}-2,2-dimethylpropionate (651729-45-2)

Conditions	Yield
Stage #1: 2-(4-tolylsulfonyl)ethyl 3-{4-[2-mercapto-5-methoxybenzimidazolyl]sulfonyl}-3,5-dimethylphenoxy-2,2-dimethylpropionate; 2-(chloromethyl)-4-methoxy-3,5-dimethylpyridine hydrochloride With potassium carbonate In DMF (N,N-dimethyl-formamide) for 1.5h; Stage #2: With hydrogenchloride at 0℃;	93%

3-[4-(2-mercapto-5-methoxy-benzimidazole-1-sulfonyl)-phenoxy]-2,2-dimethyl-propionic acid methyl ester (651729-74-7) + 2-(chloromethyl)-4-methoxy-3,5-dimethylpyridine hydrochloride (86604-75-3) → 3-[4-(5-methoxy-2-(4-methoxy-3,5-dimethyl-pyridin-2-ylmethylsulfanyl)benzimidazole-1-sulfonyl)-phenoxy]-2,2-dimethyl-propionic acid methyl ester (651729-75-8)

Conditions	Yield
With potassium carbonate In DMF (N,N-dimethyl-formamide) for 1h;	93%
With potassium carbonate In DMF (N,N-dimethyl-formamide) for 1h;	93%

2-carbamoylmethoxy-4-[{6-methoxy-2-mercaptobenzimidazolyl}sulfonyl]phenoxyacetamide (843615-34-9) + 2-(chloromethyl)-4-methoxy-3,5-dimethylpyridine hydrochloride (86604-75-3) → 1-(3,4-dimethoxycarboxamidobenzenesulfonyl)-6-methoxy-2-[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]thio-1H-benzimidazole (843615-35-0)

Conditions	Yield
With potassium carbonate In DMF (N,N-dimethyl-formamide) for 0.25h;	93%

C14H18N4OS (1319671-99-2) + 2-(chloromethyl)-4-methoxy-3,5-dimethylpyridine hydrochloride (86604-75-3) → 2-[(3,5-dimethyl-4-methoxy-pyridin-2-yl)methylthio]-6-acetylamino-5-(piperidin-1-yl)-1H-benzimidazole

Conditions	Yield
With potassium carbonate; potassium iodide In ethanol; acetone at 45℃; for 4h;	92%

(2-aminomethylpyridine) (3731-51-9) + 2-(chloromethyl)-4-methoxy-3,5-dimethylpyridine hydrochloride (86604-75-3) → 1-(4-methoxy-3,5-dimethylpyridin-2-yl)-N-((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)-N-(pyridin-2-ylmethyl)methanamine

Conditions	Yield
With tetrabutylammomium bromide; sodium carbonate In acetonitrile at 80℃; for 48h; Inert atmosphere;	92%
With potassium carbonate In acetonitrile for 72h; Inert atmosphere; Reflux;	49%
Inert atmosphere; Reflux;

3-bromo-6-hydroxy-2-methylpyridine (54923-31-8) + 2-(chloromethyl)-4-methoxy-3,5-dimethylpyridine hydrochloride (86604-75-3) → 2-{[(5-bromo-6-methylpyridin-2-yl)oxy]methyl}-4-methoxy-3,5-dimethylpyridine

Conditions	Yield
With silver carbonate In toluene at 110℃; for 6h; Darkness;	92%

potassium phtalimide (1074-82-4) + 2-(chloromethyl)-4-methoxy-3,5-dimethylpyridine hydrochloride (86604-75-3) → 2-((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)isoindoline-1,3-dione (946071-49-4)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 85℃; Inert atmosphere;	91%

2-(chloromethyl)-4-methoxy-3,5-dimethylpyridine hydrochloride (86604-75-3) → 2-chloromethyl-3,5-dimethyl-4-methoxypyridine-N-oxide (848694-10-0)

Conditions	Yield
Stage #1: 2-(chloromethyl)-4-methoxy-3,5-dimethylpyridine hydrochloride With sodium hydroxide In chloroform for 0.5h; Stage #2: With 3-chloro-benzenecarboperoxoic acid In chloroform at 55 - 60℃; for 1.5h; Further stages.;	90.4%
Stage #1: 2-(chloromethyl)-4-methoxy-3,5-dimethylpyridine hydrochloride With sodium hydrogencarbonate In chloroform Stage #2: With 3-chloro-benzenecarboperoxoic acid at 5℃; for 2.41667h; Further stages.;	52.47%

2-(chloromethyl)-4-methoxy-3,5-dimethylpyridine hydrochloride (86604-75-3) + Benzimidazol-2-thiol (134469-07-1) → 2-[(3,5-dimethyl-4-methoxy-2-pyridinylmethyl)thio]-1H-benzimidazole (73590-87-1)

Conditions	Yield
With sodium hydroxide In ethanol at 68℃; for 4h;	89.5%
With sodium hydroxide In methanol Heating;	84%

2-(chloromethyl)-4-methoxy-3,5-dimethylpyridine hydrochloride (86604-75-3) + 5-acetamido-benzimidazoline-2-thione (84445-90-9) → N-[2-(4-Methoxy-3,5-dimethyl-pyridin-2-ylmethylsulfanyl)-1H-benzoimidazol-5-yl]-acetamide (117013-90-8)

Conditions	Yield
With sodium hydroxide In ethanol; water at 90℃; for 1h;	89%

[4-(2-mercapto-6-methoxy-benzimidazole-1-sulfonyl)-phenoxy]acetic acid methyl ester (651729-82-7) + 2-(chloromethyl)-4-methoxy-3,5-dimethylpyridine hydrochloride (86604-75-3) → [4-(6-methoxy-2-(4-methoxy-3,5-dimethyl-pyridin-2-ylmethylsulfanyl)benzimidazole-1-sulfonyl)-phenoxy]acetic acid methyl ester (651729-83-8)

Conditions	Yield
With potassium carbonate In DMF (N,N-dimethyl-formamide) at 20℃; for 1.25h;	89%
With potassium carbonate In DMF (N,N-dimethyl-formamide) for 1h;	89%

3,5-diisopropylpyrazole (17536-00-4) + 2-(chloromethyl)-4-methoxy-3,5-dimethylpyridine hydrochloride (86604-75-3) → 2-[(3,5-diisopropyl-1H-pyrazol-1-yl)methyl]-4-methoxy-3,5-dimethylpyridine (1191928-12-7)

Conditions	Yield
With tetra(n-butyl)ammonium hydroxide; sodium hydroxide In water; toluene Inert atmosphere; Reflux;	89%
With tetra(n-butyl)ammonium hydroxide; sodium hydroxide In water; toluene

Upstream product

• 67-63-0 isopropyl alcohol 
• 104916-41-8 3,5-dimethyl-4-methoxy-2-cyanopyridine 
• 84006-10-0 (chloromethyl)-4-methoxy-3,5-dimethylpyridine 
• 109371-20-2 4-chloro-2,3,5-trimethylpyridine 1-oxide 
• 96300-88-8 2-Hydroxymethyl-4-methoxy-3,5-dimethylpyridine hydrochloride 
• 86604-78-6 (4-methoxy-3,5-dimethylpyridin-2-yl)methanol 
• 91219-90-8 (4-methoxy-3,5-dimethyl-pyridin-2-yl)methyl acetate 
• 86604-80-0 4-methoxy-2,3,5-trimethylpyridine 1-oxide 
• 74409-42-0 2,3,5-trimethylpyridine 1-oxide 
• 86604-79-7 2,3,5-trimethyl-4-nitropyridine N-oxide 
• 695-98-7 2,3,5-trimethyl-pyridine 

Downstream Products

• 942133-84-8 1-[2-hydroxy-4-[(4-methoxy-3,5-dimethyl-2-pyridyl)methoxy]-3-methylphenyl]ethanone 
• 848694-10-0 2-chloromethyl-3,5-dimethyl-4-methoxypyridine-N-oxide 
• 142885-92-5 5-methoxy-2-[[(4-methoxy-3,5-dimethylpyridin-2-yl-1-oxide)methyl]sulfanyl]-1H-benzimidazole 
• 113713-24-9 5-methoxy-2-((4-methoxy-3,5-dimethylpyridin-2-yl)methylthio)-1H-imidazo[4,5-b]pyridine 
• 73590-85-9 omeprazole sulfide 
• 843615-41-8 methyl 6-{2-[4-({5-methoxy-2-[(4-methoxy-3,5-dimethyl(2-Pyridyl))methylthio]benzimidazolyl}sulfonyl)phenoxy]acetylamino}hexanoate 
• 1044243-97-1 2-amino-4-chloro-8-((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)-7,8-dihydropteridin-6(5H)-one 

Relevant articles and documents

Syntheses and Crystal Structures of 2-Chloromethyl-3,5-dimethyl-4-methoxy/ethoxy-pyridines and Their Methylsulphinyl Derivatives

Abstract: Treatment of 2-(chloromethyl)-pyridine derivatives 3,5-dimethyl-4-(alkoxy)-2-(chloromethyl)-pyridine hydrochloride (alkoxy = methoxy, 1; ethoxy, 2) with 1-(4-chloro-phenyl)imidazole-2-thione in the presence of sodium methoxide afforded the corresponding methylsulphinyl derivatives 3,5-dimethyl-[4-(alkoxy)-2-pyridinyl]-methylthio-1-(4-chloro-phenyl)-imidazole (alkoxy = methoxy, 3; ethoxy, 4). Similarly, reaction of 1 or 2 with 4,6-dimethyl-pyrimidine-2-thiol gave the methylsulphinyl derivatives 3,5-dimethyl-[4-(alkoxy)-2-pyridinyl]-methylthio-4,6-dimethyl-pyrimidine (alkoxy = methoxy, 5; ethoxy, 6). While reaction of 5 with CuCl2·2H2O in methanol produced a square-planar copper(II) complex, trans-bis{3,5-dimethyl-[4-(methoxy)-2-pyridinyl]-methylthio-4,6-dimethyl-pyrimidine}-dichloro-copper(II) (7). The crystal structures of 1, 2, 4?HCl?2H2O, and 7, along with their spectroscopic properties are reported. The weak hydrogen-bonding interactions exist in compounds 1, 2, and 4?HCl?2H2O. Compound 1 crystallizes in the monoclinic space group P21/c with a = 6.074(11), b = 19.88(4), c = 9.230(16)??, β = 99.67(4)°, and Z = 4. Compound 2 crystallizes in the monoclinic space group P21/n with a = 10.0103(15), b = 7.9905(12), c = 15.120(2) ?, β = 93.924(2), and Z = 4. The unit cells of both 4?HCl?2H2O and 7 have triclinic P-1 symmetry with the cell parameters a = 7.492(8), b = 10.170(12), c = 15.723(18) ?, α = 77.159(15)°, β = 91.113(13)°, γ = 81.194(16)°, and V = 1152(2)??3 for 4?HCl?2H2O and a = 10.526(2), b = 12.936(2), c = 14.455(3)??, α = 107.929(2)°, β = 93.686(2)°, γ = 104.095(3)°, and V = 1734.3(6) ?3 for 7. Graphical Abstract: Interaction of 3,5-dimethyl-[4-(methoxy)-2-pyridinyl]-methylthio-4,6-dimethyl-pyrimidine and CuCl2·2H2O in methanol resulted in the formation of a square-planar copper(II) complex, trans-bis{3,5-dimethyl-[4-(methoxy)-2-pyridinyl]-methylthio-4,6-dimethyl-pyrimidine}-dichloro-copper(II), which was structurally characterized.

Preparation method of omeprazole intermediate

The invention relates to a preparation method of an omeprazole intermediate. According to the method, Nmethoxy-4-methoxy3, 5-dimethyl pyridinium is used as a raw material, metal ions are added as an additive, under the action of persulfate, 2-hydroxymethyl- 3, 5-dimethyl -4methoxypyridine is efficiently prepared, and then the 2-hydroxymethyl -3, 5-dimethyl- 4-methoxypyridine is further converted into 2-chloromethyl -3, 5-dimethyl- 4methoxypyridine hydrochloride. According to the method, the conversion rate, the yield and the quality of the 2-hydroxymethyl- 3, 5-dimethyl -4-methoxy pyridine areremarkably improved, so that the purity of the 2-chloromethyl- 3, 5-dimethyl- 4-methoxy pyridine hydrochloride obtained by further reaction is improved, the impurity content is reduced, the product yield and the production efficiency can be effectively improved, the production capacity is improved, and the production cost is reduced.

Preparation method of omeprazole midbody

The invention relates to a preparation method of 2-chloromethyl-3,5-dimethyl-4-methoxypyridine shown in a chemical structural formula I. The method is characterized by comprising the steps of a catalytic hydrogenation reaction, wherein Raney nickel or Pd/C is selected as a catalyst; a chlorination reaction, wherein YCln is selected from N-chloroacetamides or N-chlorosuccinimide or 1,3-dichloro-5,5-dimethylhydantoin or dichlord isocyanurice acid or symclosene; n is selected from 3 or 2 or 1; m is selected from 0 or 1 or 2.