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 558636ノート

反応式

HRID 558636 の反応式
[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]

参加物

4

反応物 2

HCID 189203694,4-Difluoro-1-(4-trifluoromethylphenyl)butane-1,3-dioneHCID 178470302HCID 178470302、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

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 27 h 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.

後処理

  1. temperaturewas refluxed for 27 h
  2. customevaporated
  3. customThe crude product was further purified by column chromatography on silica gel (ethyl acetate/heptane 7:3) and crystallization (diethyl ether/hexane)

出典と根拠

ORDレコード
ord-97f8cbdbc49845b2b5ce3d7479156d2e
出典データセット
uspto-grants-2011_11
特許番号
US08063048B2

反応ノート

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