Sodium Methoxide → 2-Methoxy-6-[2-(4-methoxy-phenyl)-ethylamino]-pyrimidine-4-carboxylic acid
반응식
C[O:2][C:3]([C:5]1[CH:10]=[C:9]([NH:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[N:8]=[C:7](Cl)[N:6]=1)=[O:4].[CH3:23][O-:24].[Na+]>CO>[CH3:23][O:24][C:7]1[N:6]=[C:5]([C:3]([OH:2])=[O:4])[CH:10]=[C:9]([NH:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[N:8]=1참가 물질
실험 절차
A mixture of 2-chloro-6-[2-(4-methoxy-phenyl)-ethylamino]-pyrimidine-4-carboxylic acid methyl ester [650 mg, 2.02 mmol, Intermediate (55)] 5M sodium methoxide in MeOH (20 mL, 10.1 mmol), in MeOH (10 mL) is heated to reflux and stirred for 5 hours. The heating is turned off and the mixture is stirred for 15 hours at room temperature and concentrated by rotary evaporator to remove the solvent. The solid is dissolved in water and the solution is acidified to pH 2 with the addition of 1N hydrochloric acid. Extracted three times with 75 mL EtOAc and concentrated the combined organic extracts to afford 2-methoxy-6-[2-(4-methoxy-phenyl)-ethylamino]-pyrimidine-4-carboxylic acid [390 mg, 64%, Intermediate (56)] as a solid. LCMS: RT=1.99 minutes, MS: 304 (M+H).
후처리
- temperatureto reflux
- stirringthe mixture is stirred for 15 hours at room temperature
- concentrationconcentrated by rotary evaporator
- customto remove the solvent
- dissolutionThe solid is dissolved in water
- additionthe solution is acidified to pH 2 with the addition of 1N hydrochloric acid
- extractionExtracted three times with 75 mL EtOAc
- concentrationconcentrated the combined organic extracts
출처 및 근거
- ORD 기록
- ord-557c665ed4244185a148ed30060b5370
- 출처 데이터셋
- uspto-grants-2009_04
- 특허 번호
- US07517889B2
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