6966-01-4

Basic information

• Product Name: Methyl 3-amino-6-bromopyrazine-2-carboxylate
• Synonyms: METHYL 3-AMINO-6-BROMOPYRAZINE-2-CARBOXYLATE;5-AMINO-2-BROMO-6-PYRAZINECARBOXYLIC ACIDMETHYL ESTER;3-Amino-6-bromopyrazine-2-carboxylic acid methyl ester;Methyl 6-Bromo-3-aminopyrazine-2-carboxylic ester;5-amino-2-bromo-6-pyrazinecarboxylicacid methyl es;5-Bromo-3-(methoxycarbonyl)pyrazin-2-amine, 2-Amino-5-bromo-3-(methoxycarbonyl)pyrazine;3-AMino-6-broMo-2-pyrazinecarboxylic acid Methyl Ester;NSC 18700
• CAS NO: 6966-01-4
• Molecular Formula: C₆H₆BrN₃O₂
• Molecular Weight: 232.03
• EINECS: 1308068-626-2
• Product Categories: Bases & Related Reagents;Heterocycles;Nucleotides
• Mol File: 6966-01-4.mol
• Article Data: 22

Chemical Properties

• Melting Point: 164-166?C
• Boiling Point: 322.422 °C at 760 mmHg
• Flash Point: 148.796 °C
• Appearance: Off-white to yellow/Solid
• Density: 1.755 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.615
• Storage Temp.: Refrigerator, Under Inert Atmosphere
• PKA: -1.74±0.10(Predicted)
• CAS DataBase Reference: Methyl 3-amino-6-bromopyrazine-2-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 3-amino-6-bromopyrazine-2-carboxylate(6966-01-4)
• EPA Substance Registry System: Methyl 3-amino-6-bromopyrazine-2-carboxylate(6966-01-4)

Safety Data

• Hazard Codes: Xi
• Statements: 43
• Safety Statements: 37
• Hazardous Substances Data: 6966-01-4(Hazardous Substances Data)

Usage

Description

Methyl 3-amino-6-bromopyrazine-2-carboxylate is a pyrazine derivative characterized by its orange solid appearance. It is a compound with a unique chemical structure that features a pyrazine ring, a methyl ester group, an amino group, and a bromine atom. This combination of functional groups endows the molecule with specific chemical properties and potential applications in various fields.

Uses

Used in Pharmaceutical Industry:
Methyl 3-amino-6-bromopyrazine-2-carboxylate is used as an Axl and C-Met receptor enzyme inhibitor for its potential role in the development of novel therapeutics. Methyl 3-amino-6-bromopyrazine-2-carboxylate's ability to inhibit these receptor enzymes makes it a promising candidate for the treatment of various diseases, including cancer, where the overactivation of these receptors is often associated with tumor growth and progression.
Used in Chemical Research:
As a pyrazine derivative, Methyl 3-amino-6-bromopyrazine-2-carboxylate is also used in chemical research for the synthesis of other complex organic molecules. Its unique structure and functional groups make it a valuable building block for the development of new compounds with diverse applications, such as pharmaceuticals, agrochemicals, and materials science.
Used in Material Science:
Methyl 3-amino-6-bromopyrazine-2-carboxylate's chemical properties, including its solid-state stability and the presence of functional groups, make it a potential candidate for use in the development of new materials with specific properties. These materials could be applied in various industries, such as electronics, where they could be used to create novel sensors or other devices with enhanced performance.

InChI:InChI=1/C6H6BrN3O2/c1-12-6(11)4-5(8)9-2-3(7)10-4/h2H,1H3,(H2,8,9)

Synthetic route

Methyl 3-amino-2-pyrazinecarboxylate (16298-03-6) → methyl 3-amino-6-bromopyrazine-2-carboxylate (6966-01-4)

Conditions	Yield
With N-Bromosuccinimide In acetonitrile for 2h; Heating / reflux;	100%
With bromine; acetic acid In water	94%
Stage #1: Methyl 3-amino-2-pyrazinecarboxylate With bromine; acetic acid at 45℃; for 0.833333h; Stage #2: With water at 20℃; for 0.5h;	94%

methanol (67-56-1) + 3-amino-6-bromo-pyrazine-2-carboxylic acid (486424-37-7) → methyl 3-amino-6-bromopyrazine-2-carboxylate (6966-01-4)

Conditions	Yield
With sulfuric acid at 0 - 40℃; for 48h;	80.1%
With sulfuric acid In water

3-aminopyrazinoic acid (5424-01-1) → methyl 3-amino-6-bromopyrazine-2-carboxylate (6966-01-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: sulfuric acid 2: bromine; acetic acid View Scheme
Multi-step reaction with 2 steps 1: sulfuric acid / 20 °C / Cooling with ice 2: N-Bromosuccinimide / acetonitrile / 20 °C View Scheme
Multi-step reaction with 2 steps 1: sulfuric acid / 48 h / Cooling with ice 2: N-Bromosuccinimide / acetonitrile / 24 h / 20 °C / Inert atmosphere View Scheme

methyl 3-amino-6-bromopyrazine-2-carboxylate (6966-01-4) → 3-amino-6-bromopyrazine-2-carbohydrazide (1225062-23-6)

Conditions	Yield
With hydrazine hydrate In ethanol at 50℃; for 40h; Inert atmosphere;	100%
With hydrazine hydrate In ethanol at 50℃; for 40h; Inert atmosphere;	100%
With hydrazine hydrate In ethanol at 50℃; for 40h; Inert atmosphere;	100%

methyl 3-amino-6-bromopyrazine-2-carboxylate (6966-01-4) → 3-amino-6-bromopyrazine-2-carboxylic acid sodium salt

Conditions	Yield
With sodium hydroxide In water Reflux;	100%

methyl 3-amino-6-bromopyrazine-2-carboxylate (6966-01-4) → 3-amino-6-bromo-pyrazine-2-carboxylic acid (486424-37-7)

Conditions	Yield
Stage #1: methyl 3-amino-6-bromopyrazine-2-carboxylate With water; lithium hydroxide In methanol at 90℃; for 5h; Stage #2: With hydrogenchloride In methanol; water	99%
With sodium hydroxide In ethanol	90%
With lithium hydroxide In methanol; water for 2h; Reflux;	83%

methyl 3-amino-6-bromopyrazine-2-carboxylate (6966-01-4) + 2-Methoxyphenylboronic acid (5720-06-9) → methyl 3-amino-6-(2-methoxyphenyl)pyrazine-2-carboxylate

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In 1,4-dioxane; water at 100℃; Inert atmosphere;	99%

methyl 3-amino-6-bromopyrazine-2-carboxylate (6966-01-4) + aniline (62-53-3) → 3-amino-6-bromo-N-phenyl-pyrazine-2-carboxamide (36204-92-9)

Conditions	Yield
at 115℃; for 4h; Microwave irradiation;	98%

4-(isopropylsulfonyl)phenylboronic acid + methyl 3-amino-6-bromopyrazine-2-carboxylate (6966-01-4) → methyl 3-amino-6-(4-(isopropylsulfonyl)phenyl)pyrazine-2-carboxylate

Conditions	Yield
With potassium phosphate; bis(tri-t-butylphosphine)palladium(0) In water; acetonitrile at 20 - 60℃; for 2h; Suzuki Coupling;	97%

methyl 3-amino-6-bromopyrazine-2-carboxylate (6966-01-4) + 4-methoxyphenylboronic acid (5720-07-0) → 3-Amino-6-(4-methoxy-phenyl)-pyrazine-2-carboxylic acid methyl ester (113892-84-5)

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; triethylamine In N,N-dimethyl-formamide at 90℃; for 12h;	94%

methyl 3-amino-6-bromopyrazine-2-carboxylate (6966-01-4) + di-tert-butyl dicarbonate (24424-99-5) → methyl 3-(bis(tert-butoxycarbonyl)amino)-6-bromopyrazine-2-carboxylate (1225064-15-2)

Conditions	Yield
With dmap In 1,2-dichloro-ethane at 20 - 75℃; for 18.5h; Product distribution / selectivity; Inert atmosphere;	94%
dmap In 1,2-dichloro-ethane at 20 - 75℃; Product distribution / selectivity; Inert atmosphere;	94%

methyl 3-amino-6-bromopyrazine-2-carboxylate (6966-01-4) + Cyclopentamine (1003-03-8) → 3-amino-6-bromo-N-cyclopentylpyrazine-2-carboxamide

Conditions	Yield
at 180℃; for 4h; Microwave irradiation;	93%

methyl 3-amino-6-bromopyrazine-2-carboxylate (6966-01-4) → 3-hydroxy-6-bromopyrazine-2-carboxylic acid methyl ester (21874-61-3)

Conditions	Yield
Stage #1: methyl 3-amino-6-bromopyrazine-2-carboxylate With sulfuric acid; sodium nitrite at -5 - 25℃; for 2h; Stage #2: With water for 1.5h;	92.7%
With sulfuric acid; sodium nitrite at -5 - 20℃; for 2h;	90%
With sulfuric acid; sodium nitrite at 0 - 60℃; for 0.5h; Reagent/catalyst;	85%

methyl 3-amino-6-bromopyrazine-2-carboxylate (6966-01-4) + benzylamine (100-46-9) → 3-amino-6-bromo-N-benzylpyrazine-2-carboxamide

Conditions	Yield
at 115℃; for 4h; Microwave irradiation;	92%

methyl 3-amino-6-bromopyrazine-2-carboxylate (6966-01-4) + 4-methanesulphonylphenylboronic acid (149104-88-1) → 3-amino-6-(4-(methylsulfonyl)phenyl)pyrazine-2-carboxylic acid (1232423-29-8)

Conditions	Yield
Stage #1: methyl 3-amino-6-bromopyrazine-2-carboxylate; 4-methanesulphonylphenylboronic acid With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,2-dimethoxyethane at 90℃; for 9h; Stage #2: With hydrogenchloride In water pH=1;	91%

methyl 3-amino-6-bromopyrazine-2-carboxylate (6966-01-4) + 2,6-difluorophenylboronic acid (162101-25-9) → methyl 3-amino-6-(2,6-difluorophenyl)pyrazine-2-carboxylate (1620013-45-7)

Conditions	Yield
With bis(tri-t-butylphosphine)palladium(0); N-ethyl-N,N-diisopropylamine In 1,4-dioxane; water at 100℃; for 14h; Inert atmosphere; Sealed tube;	91%

methyl 3-amino-6-bromopyrazine-2-carboxylate (6966-01-4) + ethanolamine (141-43-5) → 3-amino-6-bromo-N-(2-hydroxyethyl)pyrazine-2-carboxamide

Conditions	Yield
at 115℃; for 4h; Microwave irradiation;	91%

methyl 3-amino-6-bromopyrazine-2-carboxylate (6966-01-4) + tert-butyl 3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]sulfonylpiperidine-1-carboxylate (1427750-91-1) → methyl 3-amino-6-[4-[(1-tert-butoxycarbonyl-3-piperidyl)sulfonyl]phenyl]pyrazine-2-carboxylate (1432755-73-1)

Conditions	Yield
With potassium phosphate; bis(tri-t-butylphosphine)palladium(0) at 60℃; for 2h; Inert atmosphere;	90.02%

methyl 3-amino-6-bromopyrazine-2-carboxylate (6966-01-4) + methylamine (74-89-5) → 3-amino-6-bromo-N-methylpyrazine-2-carboxamide (146940-37-6)

Conditions	Yield
In water at 20℃;	90%
In water at 20℃; for 7h;	90%
In water at 20℃; for 4h;	90%
at 115℃; for 4h; Microwave irradiation;	53%
In water for 1.5h; Ambient temperature;

(2-ethoxypyridin-3-yl)boronic acid (854373-97-0) + methyl 3-amino-6-bromopyrazine-2-carboxylate (6966-01-4) → 3-amino-6-(2-ethoxy-pyridin-3-yl)-pyrazine-2-carboxylic acid methyl ester

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,4-dioxane; water at 20℃; for 16h; Suzuki cross-coupling;	90%

methyl 3-amino-6-bromopyrazine-2-carboxylate (6966-01-4) + bis(pinacol)diborane (73183-34-3) → methyl 3-amino-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyrazinecarboxylate

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 80℃; for 18h; Time; Inert atmosphere;	90%

methyl 3-amino-6-bromopyrazine-2-carboxylate (6966-01-4) + furan-3-boronic acid (55552-70-0) → 3-amino-6-(furan-3-yl)-pyrazine-2-carboxylic acid methyl ester (113892-86-7)

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; triethylamine In N,N-dimethyl-formamide at 90℃; for 12h;	89%
Stage #1: methyl 3-amino-6-bromopyrazine-2-carboxylate With 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate In N,N-dimethyl-formamide at 20 - 50℃; for 0.25h; Stage #2: furan-3-boronic acid With triethylamine In N,N-dimethyl-formamide at 90℃; for 16h;	61.8%
With triethylamine; 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate In N,N-dimethyl-formamide at 90℃; for 16h; Inert atmosphere;	61.8%
With potassium acetate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane at 170℃; for 0.333333h; Microwave irradiation;

pyrrolidine (123-75-1) + methyl 3-amino-6-bromopyrazine-2-carboxylate (6966-01-4) → (3-amino-6-bromopyrazin-2-yl)(pyrrolidin-1-yl)methanone

Conditions	Yield
at 115℃; for 4h; Microwave irradiation;	89%

methyl 3-amino-6-bromopyrazine-2-carboxylate (6966-01-4) + benzo[b]thiophen-3-yl-3-boronic acid (113893-08-6) → 3-Amino-6-benzo[b]thiophen-3-yl-pyrazine-2-carboxylic acid methyl ester (113892-85-6)

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; triethylamine In N,N-dimethyl-formamide at 90℃; for 12h;	87%

SEC-BUTYLAMINE (33966-50-6) + methyl 3-amino-6-bromopyrazine-2-carboxylate (6966-01-4) → 3-amino-6-bromo-N-(sec-butyl)-pyrazine-2-carboxamide

Conditions	Yield
at 100℃; for 6h; Microwave irradiation;	87%

methyl 3-amino-6-bromopyrazine-2-carboxylate (6966-01-4) + Trimethylboroxine (823-96-1) → methyl 3-amino-6-methylpyrazine-2-carboxylate (2032-84-0)

Conditions	Yield
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); potassium carbonate In 1,2-dimethoxyethane at 100℃; for 16h; Inert atmosphere; Sealed tube;	87%

methyl 3-amino-6-bromopyrazine-2-carboxylate (6966-01-4) + (2,3-dimethoxypyridin-4-yl)boronic acid (1031438-93-3) → methyl 3-amino-6-(2,3-dimethoxypyridin-4-yl)pyrazine-2-carboxylate (1031439-07-2)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,4-dioxane; water for 0.25h; Suzuki-Miyaura cross-coupling; Reflux;	86%

methyl 3-amino-6-bromopyrazine-2-carboxylate (6966-01-4) → lithium 3-amino-6-bromopyrazine-2-carboxylate

Conditions	Yield
With water; lithium hydroxide In methanol at 20 - 50℃; for 3.08333h;	85%

methyl 3-amino-6-bromopyrazine-2-carboxylate (6966-01-4) + 3-Diethylboranylpyridine (89878-14-8) → 3-amino-6-(pyridin-3-yl)pyrazine-2-carboxylic acid (1232423-31-2)

Conditions	Yield
Stage #1: methyl 3-amino-6-bromopyrazine-2-carboxylate; 3-Diethylboranylpyridine With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,2-dimethoxyethane; water at 80℃; Suzuki coupling; Stage #2: With acetic acid In water pH=5;	84%

methyl 3-amino-6-bromopyrazine-2-carboxylate (6966-01-4) + methyl 3-amino-5-<(ethoxycarbonyl)methyl>-6-chloropyrazinoate (113892-80-1) → 3-Amino-5-ethoxycarbonylmethyl-6-phenyl-pyrazine-2-carboxylic acid methyl ester (113892-87-8)

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; triethylamine In N,N-dimethyl-formamide at 90℃; for 12h;	82%

methyl 3-amino-6-bromopyrazine-2-carboxylate (6966-01-4) + phenylboronic acid (98-80-6) → methyl 3-amino-6-phenyl-2-pyrazine carboxylate (1503-42-0)

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; triethylamine In N,N-dimethyl-formamide at 90℃; for 12h;	82%
Stage #1: 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate In DMF (N,N-dimethyl-formamide) at 50℃; for 0.333333h; Stage #2: methyl 3-amino-6-bromopyrazine-2-carboxylate; phenylboronic acid With triethylamine In ISOPROPYLAMIDE at 20 - 90℃; for 12h;
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In methanol; water; toluene at 85℃; for 4h; Inert atmosphere;

(4-(pyrrolidin-1-ylsulfonyl)phenyl)boronic acid (486422-57-5) + methyl 3-amino-6-bromopyrazine-2-carboxylate (6966-01-4) → methyl 3-amino-6-[4-(pyrrolidin-1-ylsulfonyl)phenyl]pyrazine-2-carboxylate (486423-09-0)

Conditions	Yield
With potassium phosphate tribasic; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,2-dimethoxyethane; water at 160℃; for 0.5h; heating in a microwave oven;	82%
With potassium phosphate tribasic; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,2-dimethoxyethane; water at 160℃; for 0.166667h; microwave oven;	82%

Upstream product

• 16298-03-6 Methyl 3-amino-2-pyrazinecarboxylate 
• 67-56-1 methanol 
• 486424-37-7 3-amino-6-bromo-pyrazine-2-carboxylic acid 
• 5424-01-1 3-aminopyrazinoic acid 

Downstream Products

• 486424-37-7 3-amino-6-bromo-pyrazine-2-carboxylic acid 
• 113892-84-5 3-Amino-6-(4-methoxy-phenyl)-pyrazine-2-carboxylic acid methyl ester 
• 135673-75-5 3-Amino-5-benzoyl-6-bromo-pyrazine-2-carboxylic acid methyl ester 
• 113892-87-8 3-Amino-5-ethoxycarbonylmethyl-6-phenyl-pyrazine-2-carboxylic acid methyl ester 
• 1503-42-0 methyl 3-amino-6-phenyl-2-pyrazine carboxylate 
• 486423-09-0 methyl 3-amino-6-[4-(pyrrolidin-1-ylsulfonyl)phenyl]pyrazine-2-carboxylate 
• 1100094-90-3 3-amino-6-(4-hydroxy-3-methoxyphenyl)pyrazine-2-carboxylic acid 
• 1313913-56-2 C₂₃H₂₆N₆O₃ 
• 1313913-57-3 C₂₄H₂₉N₇O₃ 
• 1313913-58-4 C₂₃H₂₈N₆O₃ 
• 1313913-35-7 C₂₅H₂₈N₄O₅ 
• 1313913-36-8 C₂₄H₂₆N₄O₄ 
• 1313913-37-9 C₂₅H₂₉N₅O₄ 
• 1313913-38-0 C₂₄H₂₈N₄O₄ 

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