4,4-Difluoro-1-(4-trifluoromethylphenyl)butane-1,3-dione → 4-Difluoromethyl-2-(4-trifluoromethyl-phenyl)-imidazo[1,5-a]pyrimidine-8-carboxylic acid ethyl ester

HRID 1293745노트

반응식

HRID 1293745 반응식
[F:1][CH:2]([F:18])[C:3](=O)[CH2:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=1)=O.[CH2:19]([O:21][C:22]([C:24]1[N:25]=[CH:26][NH:27][C:28]=1[NH2:29])=[O:23])[CH3:20]>C(O)(=O)C>[CH2:19]([O:21][C:22]([C:24]1[N:25]=[CH:26][N:27]2[C:3]([CH:2]([F:18])[F:1])=[CH:4][C:5]([C:7]3[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=3)=[N:29][C:28]=12)=[O:23])[CH3:20]

참가 물질

4

반응물 2

HCID 189203694,4-Difluoro-1-(4-trifluoromethylphenyl)butane-1,3-dioneHCID 178470302HCID 178470302, 화합물

생성물 1

HCID 670008454-Difluoromethyl-2-(4-trifluoromethyl-phenyl)-imidazo[1,5-a]pyrimidine-8-carboxylic acid ethyl ester수율 49.5%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

A mixture of 4,4-difluoro-1-(4-trifluoromethyl-phenyl)-butane-1,3-dione (8.87 g, 33.3 mmol) and 5-amino-1H-imidazole-4-carboxylic acid ethyl ester (5.17 g, 33.3 mmol) in acetic acid (100 ml) was refluxed for 27h and evaporated. The crude product was further purified by column chromatography on silica gel (ethyl acetate/heptane 7:3) and crystallization (diethyl ether/hexane) to yield 4-difluoromethyl-2-(4-trifluoromethyl-phenyl)-imidazo[1,5-a]pyrimidine-8-carboxylic acid ethyl ester (6.35 g, 49%) as a yellow solid. MS (EI) 385.1 [(M)+]; mp 219° C.

후처리

  1. customevaporated
  2. customThe crude product was further purified by column chromatography on silica gel (ethyl acetate/heptane 7:3) and crystallization (diethyl ether/hexane)

출처 및 근거

ORD 기록
ord-497b60418fd24eb193d1296861f1f041
출처 데이터셋
uspto-grants-2007_07
특허 번호
US07238808B2

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