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CAS No.: | 146464-90-6 |
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Name: | α-propargylhomoterephthalic acid dimethyl ester |
Article Data: | 11 |
Molecular Structure: | |
Formula: | C14H14O4 |
Molecular Weight: | 246.263 |
Synonyms: | α-propargylhomoterephthalic acid dimethyl ester;Benzeneacetic acid, 4-(methoxycarbonyl)-.alpha.-2-propyn-1-yl-, methyl ester;Methyl 4-(1-Methoxy-1-oxopent-4-yn-2-yl) benzoate;Benzeneacetic acid, 4-(Methoxycarbonyl)-α-2-propyn-1-yl-, Methyl ester;4-(Methoxycarbonyl)-alpha-2-propynyl-benzeneacetic acid methyl ester |
Density: | 1.149±0.06 g/cm3(Predicted) |
Boiling Point: | 348.2±32.0 °C(Predicted) |
PSA: | 52.60000 |
LogP: | 1.75310 |
methyl 4-(2-methoxy-2-oxoethyl)benzoate
propargyl bromide
α-propargylhomoterephthalic acid dimethyl ester
Conditions | Yield |
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Stage #1: methyl 4-(2-methoxy-2-oxoethyl)benzoate; propargyl bromide In tetrahydrofuran at -10℃; Inert atmosphere; Stage #2: With lithium hexamethyldisilazane In tetrahydrofuran at -10℃; Temperature; Solvent; Reagent/catalyst; | 87% |
Stage #1: methyl 4-(2-methoxy-2-oxoethyl)benzoate With sodium hydride In tetrahydrofuran at 0 - 15℃; Autoclave; Stage #2: propargyl bromide In tetrahydrofuran at -20 - 10℃; for 5h; | 64.5% |
With potassium hydride 1.) THF, 0 deg C, 1 h, 2.) THF, a0) o deg C, 30 min, b) RT, 16 h; Yield given. Multistep reaction; |
methyl 4-(2-methoxy-2-oxoethyl)benzoate
propargyl bromide
A
dipropargyl homoterephthalic acid dimethyl ester
B
α-propargylhomoterephthalic acid dimethyl ester
Conditions | Yield |
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With tetra-(n-butyl)ammonium iodide; potassium carbonate In N,N-dimethyl acetamide at 25 - 30℃; for 26h; Concentration; | A n/a B 65.6% |
Stage #1: methyl 4-(2-methoxy-2-oxoethyl)benzoate With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 1h; Stage #2: propargyl bromide In tetrahydrofuran; mineral oil at 0 - 20℃; for 17h; | |
With tetra-(n-butyl)ammonium iodide; potassium carbonate In N,N-dimethyl acetamide at 25 - 30℃; Concentration; |
propargyl bromide
A
dipropargyl homoterephthalic acid dimethyl ester
B
α-propargylhomoterephthalic acid dimethyl ester
Conditions | Yield |
---|---|
Stage #1: methyl 4-(2-methoxy-2-oxoethyl)benzoate With sodium hydride In tetrahydrofuran at 0℃; for 1h; Stage #2: propargyl bromide In tetrahydrofuran at 0 - 20℃; for 17h; Stage #3: With acetic acid In tetrahydrofuran |
4-(carboxymethyl)benzoic acid
α-propargylhomoterephthalic acid dimethyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: toluene-4-sulfonic acid / 24 h / Reflux; Autoclave 2.1: sodium hydride / tetrahydrofuran / 0 - 15 °C / Autoclave 2.2: 5 h / -20 - 10 °C View Scheme |
α-propargylhomoterephthalic acid dimethyl ester
methyl-4-(2-((2,4-diaminopteridin-6-yl)methyl)-1-methoxy-1-oxopent-4-yn-2-yl)benzoate
Conditions | Yield |
---|---|
Stage #1: α-propargylhomoterephthalic acid dimethyl ester With sodium hydride In N,N-dimethyl-formamide at -5 - 0℃; for 1.5h; Stage #2: C8H9BrN6*BrH In N,N-dimethyl-formamide at -25 - 20℃; for 5h; | 85% |
6-bromomethyl-2,4-diaminopteridine hydrobromide
α-propargylhomoterephthalic acid dimethyl ester
10-propargyl-10-carbomethoxy-4-deoxy-4-amino-10-deazapteroic acid methyl ester hydrobromide salt
Conditions | Yield |
---|---|
Stage #1: 6-bromomethyl-2,4-diaminopteridine hydrobromide; α-propargylhomoterephthalic acid dimethyl ester With sodium hydride In N,N-dimethyl acetamide at -20 - -10℃; Stage #2: With hydrogen bromide In methanol; dichloromethane; water; isopropyl alcohol at 0 - 5℃; Concentration; | 73.7% |
6-bromomethyl-2,4-diaminopteridine hydrobromide
α-propargylhomoterephthalic acid dimethyl ester
methyl-4-(2-((2,4-diaminopteridin-6-yl)methyl)-1-methoxy-1-oxopent-4-yn-2-yl)benzoate
Conditions | Yield |
---|---|
With potassium hydride 1.) DMF, 0 deg C, 30 min, 2.) DMF, 2-propanol, 10 deg C, 2,5 h; Multistep reaction; | |
Stage #1: α-propargylhomoterephthalic acid dimethyl ester With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 5℃; Stage #2: 6-bromomethyl-2,4-diaminopteridine hydrobromide In N,N-dimethyl-formamide; mineral oil at -25 - 20℃; for 6h; | |
With sodium hydride In N,N-dimethyl acetamide at -20 - -10℃; Concentration; |
2,4-diamino-5-methyl-6-(bromomethyl)pyrido<2,3-d>pyrimidine
α-propargylhomoterephthalic acid dimethyl ester
4-[1-(2,4-Diamino-5-methyl-pyrido[2,3-d]pyrimidin-6-ylmethyl)-1-methoxycarbonyl-but-3-ynyl]-benzoic acid methyl ester
Conditions | Yield |
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With sodium hydride 1.) DMF, 0 deg C, 0.5 h, 2.) DMF, from -25 deg C to 25 deg C; Yield given. Multistep reaction; |
α-propargylhomoterephthalic acid dimethyl ester
4-[1-(2,4-Diamino-5-methyl-pyrido[2,3-d]pyrimidin-6-ylmethyl)-but-3-ynyl]-benzoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 1.) NaH / 1.) DMF, 0 deg C, 0.5 h, 2.) DMF, from -25 deg C to 25 deg C 2: 74 percent / 4N NaOH / dimethylsulfoxide / 96 h / 20 - 60 °C 3: 89 percent / dimethylsulfoxide / 0.83 h / 105 - 110 °C View Scheme |
α-propargylhomoterephthalic acid dimethyl ester
4-[1-Carboxy-1-(2,4-diamino-5-methyl-pyrido[2,3-d]pyrimidin-6-ylmethyl)-but-3-ynyl]-benzoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 1.) NaH / 1.) DMF, 0 deg C, 0.5 h, 2.) DMF, from -25 deg C to 25 deg C 2: 74 percent / 4N NaOH / dimethylsulfoxide / 96 h / 20 - 60 °C View Scheme |