α-propargylhomoterephthalic acid dimethyl ester CAS:146464-90-6 Qingdao Belugas Import and Export Co., Ltd. is a scientific and technological company integrating research and development, production and trade of chemical intermediates, special
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inquirymethyl 4-(2-methoxy-2-oxoethyl)benzoate
propargyl bromide
α-propargylhomoterephthalic acid dimethyl ester
Conditions | Yield |
---|---|
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 |
---|---|
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 |
---|---|
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 |
α-propargylhomoterephthalic acid dimethyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 4 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 4: Et3N / dimethylformamide / 0.25 h / 20 - 25 °C View Scheme |
α-propargylhomoterephthalic acid dimethyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 5 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 4: Et3N / dimethylformamide / 0.25 h / 20 - 25 °C 5: dimethylformamide / 0.5 h View Scheme |
α-propargylhomoterephthalic acid dimethyl ester
4-(1-(2,4-diaminopteridin-6-yl)pent-4-yn-2-yl)benzoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 1.) KH / 1.) DMF, 0 deg C, 30 min, 2.) DMF, 2-propanol, 10 deg C, 2,5 h 2: 10percent aq. NaOH / 2-methoxy-ethanol; H2O / 4 h / Ambient temperature 3: dimethylsulfoxide / 0.08 h / 120 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0 - 5 °C 1.2: 6 h / -25 - 20 °C 2.1: sodium hydroxide; water / 2-methoxy-ethanol / 4 h / 20 °C 3.1: dimethyl sulfoxide / 0.17 h / 115 - 120 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.75 h / -5 - 0 °C 1.2: 2.5 h / -25 - -20 °C 2.1: water; sodium hydroxide / 2-methoxy-ethanol / 4 h / 15 - 20 °C 3.1: dimethyl sulfoxide / 0.75 h / 120 - 125 °C 3.2: 24 h / 20 °C View Scheme | |
Multi-step reaction with 4 steps 1: sodium hydride / N,N-dimethyl acetamide / -20 - -10 °C 2: hydrogen bromide / methanol; isopropyl alcohol; dichloromethane; water / 0 - 5 °C 3: potassium hydroxide / water; 2-methoxy-ethanol / 6 h / 25 - 30 °C 4: dimethyl sulfoxide / 110 - 115 °C View Scheme | |
Multi-step reaction with 5 steps 1: sodium hydride / N,N-dimethyl acetamide / -20 - -10 °C 2: hydrogen bromide / methanol; isopropyl alcohol; dichloromethane; water / 0 - 5 °C 3: potassium hydroxide / water; 2-methoxy-ethanol / 6 h / 25 - 30 °C 4: methanol / 0 - 5 °C 5: N,N-dimethyl acetamide / 1 h / 50 - 110 °C View Scheme |
α-propargylhomoterephthalic acid dimethyl ester
4-(2-carboxy-1-(2,4-diaminopteridin-6-yl)pent-4-yn-2-yl)benzoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 1.) KH / 1.) DMF, 0 deg C, 30 min, 2.) DMF, 2-propanol, 10 deg C, 2,5 h 2: 10percent aq. NaOH / 2-methoxy-ethanol; H2O / 4 h / Ambient temperature View Scheme | |
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0 - 5 °C 1.2: 6 h / -25 - 20 °C 2.1: sodium hydroxide; water / 2-methoxy-ethanol / 4 h / 20 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl acetamide / -20 - -10 °C 1.2: 0 - 5 °C 2.1: potassium hydroxide / water / 4 h / 20 - 25 °C 2.2: 15 h / 20 - 25 °C View Scheme |
α-propargylhomoterephthalic acid dimethyl ester
C23H24N6O4
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 1.) KH / 1.) DMF, 0 deg C, 30 min, 2.) DMF, 2-propanol, 10 deg C, 2,5 h 2: 10percent aq. NaOH / 2-methoxy-ethanol; H2O / 4 h / Ambient temperature 3: dimethylsulfoxide / 0.08 h / 120 °C 4: Et3N / dimethylformamide / 1 h / Ambient temperature View Scheme |
α-propargylhomoterephthalic acid dimethyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: 1.) KH / 1.) DMF, 0 deg C, 30 min, 2.) DMF, 2-propanol, 10 deg C, 2,5 h 2: 10percent aq. NaOH / 2-methoxy-ethanol; H2O / 4 h / Ambient temperature 3: dimethylsulfoxide / 0.08 h / 120 °C 4: Et3N / dimethylformamide / 1 h / Ambient temperature 5: Et3N / dimethylformamide / 2 h / Ambient temperature 6: 10percent aq. NaOH / 2-methoxy-ethanol; H2O / 2 h / Ambient temperature View Scheme | |
Multi-step reaction with 5 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0 - 5 °C 1.2: 6 h / -25 - 20 °C 2.1: sodium hydroxide; water / 2-methoxy-ethanol / 4 h / 20 °C 3.1: dimethyl sulfoxide / 0.17 h / 115 - 120 °C 4.1: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 3 h / 20 - 25 °C 5.1: sodium hydroxide; methanol / 8 h / 20 - 25 °C 5.2: 24 h / 20 - 25 °C 5.3: pH 4 View Scheme | |
Multi-step reaction with 5 steps 1.1: 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; sodium hydride / mineral oil / 0.5 h / -10 - 0 °C 1.2: -5 - 20 °C 2.1: sodium hydroxide; water / isopropyl alcohol / 20 °C 2.2: pH 7.5 3.1: triethylamine / 1-methyl-pyrrolidin-2-one / 1 h / 120 - 130 °C 3.2: 0 - 20 °C 4.1: triethylamine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / N,N-dimethyl-formamide / 20 °C 5.1: sodium hydroxide; water / methanol / 15 - 20 °C 5.2: pH 7 - 8 View Scheme |
α-propargylhomoterephthalic acid dimethyl ester
10-propargyl-10-deazaaminopterin diethyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 1.) KH / 1.) DMF, 0 deg C, 30 min, 2.) DMF, 2-propanol, 10 deg C, 2,5 h 2: 10percent aq. NaOH / 2-methoxy-ethanol; H2O / 4 h / Ambient temperature 3: dimethylsulfoxide / 0.08 h / 120 °C 4: Et3N / dimethylformamide / 1 h / Ambient temperature 5: Et3N / dimethylformamide / 2 h / Ambient temperature View Scheme | |
Multi-step reaction with 4 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.75 h / -5 - 0 °C 1.2: 2.5 h / -25 - -20 °C 2.1: water; sodium hydroxide / 2-methoxy-ethanol / 4 h / 15 - 20 °C 3.1: dimethyl sulfoxide / 0.75 h / 120 - 125 °C 3.2: 24 h / 20 °C 4.1: triethylamine; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / N,N-dimethyl-formamide / 1 h / -5 - 0 °C 4.2: 2 h / -15 - -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 |
---|---|
In N-methyl-acetamide |
α-propargylhomoterephthalic acid dimethyl ester
10-propargyl-10-deazaaminopterin dimethyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0 - 5 °C 1.2: 6 h / -25 - 20 °C 2.1: sodium hydroxide; water / 2-methoxy-ethanol / 4 h / 20 °C 3.1: dimethyl sulfoxide / 0.17 h / 115 - 120 °C 4.1: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 3 h / 20 - 25 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; sodium hydride / mineral oil / 0.5 h / -10 - 0 °C 1.2: -5 - 20 °C 2.1: sodium hydroxide; water / isopropyl alcohol / 20 °C 2.2: pH 7.5 3.1: triethylamine / 1-methyl-pyrrolidin-2-one / 1 h / 120 - 130 °C 3.2: 0 - 20 °C 4.1: triethylamine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / N,N-dimethyl-formamide / 20 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: sodium hydride / N,N-dimethyl acetamide / -20 - -10 °C 1.2: 0 - 5 °C 2.1: potassium hydroxide / water / 4 h / 20 - 25 °C 2.2: 15 h / 20 - 25 °C 3.1: dimethyl sulfoxide / 110 - 115 °C 3.2: 50 - 55 °C 4.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl acetamide / 0.5 h / 0 - 5 °C / Inert atmosphere 4.2: 21 h / 0 - 25 °C View Scheme |
α-propargylhomoterephthalic acid dimethyl ester
A
C25H27N7O5
B
C25H27N7O5
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0 - 5 °C 1.2: 6 h / -25 - 20 °C 2.1: sodium hydroxide; water / 2-methoxy-ethanol / 4 h / 20 °C 3.1: dimethyl sulfoxide / 0.17 h / 115 - 120 °C 4.1: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 3 h / 20 - 25 °C 5.1: CHIRALPAK AD 20μ, 11 cm id.x.27 cm L / ethanol / 30 °C View Scheme |
6-bromomethyl-pteridine-2,4-diamine
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 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; sodium hydride In mineral oil at -10 - 0℃; for 0.5h; Stage #2: 6-bromomethyl-pteridine-2,4-diamine In mineral oil at -5 - 20℃; | 40.2 g |
Stage #1: α-propargylhomoterephthalic acid dimethyl ester With sodium hydride In N,N-dimethyl-formamide at -5 - 0℃; for 0.75h; Stage #2: 6-bromomethyl-pteridine-2,4-diamine In N,N-dimethyl-formamide at -25 - -20℃; for 2.5h; |
α-propargylhomoterephthalic acid dimethyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; sodium hydride / mineral oil / 0.5 h / -10 - 0 °C 1.2: -5 - 20 °C 2.1: sodium hydroxide; water / isopropyl alcohol / 20 °C 2.2: pH 7.5 View Scheme |
α-propargylhomoterephthalic acid dimethyl ester
10-propargyl-10-carboxy-4-deoxy-4-amino-10-deazapteroic acid sodium salt
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; sodium hydride / mineral oil / 0.5 h / -10 - 0 °C 1.2: -5 - 20 °C 2.1: sodium hydroxide; water / isopropyl alcohol / 20 °C 2.2: pH 7.5 3.1: triethylamine / 1-methyl-pyrrolidin-2-one / 1 h / 120 - 130 °C 3.2: 0 - 20 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: sodium hydride / N,N-dimethyl acetamide / -20 - -10 °C 1.2: 0 - 5 °C 2.1: potassium hydroxide / water / 4 h / 20 - 25 °C 2.2: 15 h / 20 - 25 °C 3.1: dimethyl sulfoxide / 110 - 115 °C 3.2: 50 - 55 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: sodium hydride / N,N-dimethyl acetamide / -20 - -10 °C 1.2: 0 - 5 °C 2.1: potassium hydroxide / water / 4 h / 20 - 25 °C 2.2: 15 h / 20 - 25 °C 3.1: methanol / 0 - 5 °C 4.1: N,N-dimethyl acetamide / 1 h / 50 - 110 °C 4.2: 0 - 15 °C View Scheme | |
Multi-step reaction with 5 steps 1: sodium hydride / N,N-dimethyl acetamide / -20 - -10 °C 2: hydrogen bromide / methanol; isopropyl alcohol; dichloromethane; water / 0 - 5 °C 3: potassium hydroxide / water; 2-methoxy-ethanol / 6 h / 25 - 30 °C 4: dimethyl sulfoxide / 110 - 115 °C 5: sodium hydroxide / water / 0 - 15 °C View Scheme | |
Multi-step reaction with 6 steps 1: sodium hydride / N,N-dimethyl acetamide / -20 - -10 °C 2: hydrogen bromide / methanol; isopropyl alcohol; dichloromethane; water / 0 - 5 °C 3: potassium hydroxide / water; 2-methoxy-ethanol / 6 h / 25 - 30 °C 4: methanol / 0 - 5 °C 5: N,N-dimethyl acetamide / 1 h / 50 - 110 °C 6: sodium hydroxide / water / 0 - 15 °C View Scheme |
α-propargylhomoterephthalic acid dimethyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: sodium hydride / N,N-dimethyl acetamide / -20 - -10 °C 1.2: 0 - 5 °C 2.1: potassium hydroxide / water / 4 h / 20 - 25 °C 2.2: 15 h / 20 - 25 °C 3.1: methanol / 0 - 5 °C View Scheme | |
Multi-step reaction with 4 steps 1: sodium hydride / N,N-dimethyl acetamide / -20 - -10 °C 2: hydrogen bromide / methanol; isopropyl alcohol; dichloromethane; water / 0 - 5 °C 3: potassium hydroxide / water; 2-methoxy-ethanol / 6 h / 25 - 30 °C 4: methanol / 0 - 5 °C View Scheme |
α-propargylhomoterephthalic acid dimethyl ester
10-propargyl-10-carbomethoxy-4-deoxy-4-amino-10-deazapteroic acid methyl ester hydrobromide salt
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: sodium hydride / N,N-dimethyl acetamide / -20 - -10 °C 2: hydrogen bromide / methanol; isopropyl alcohol; dichloromethane; water / 0 - 5 °C View Scheme |
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