Water → 4-Trifluoromethyl-2-(4-trifluoromethyl-phenyl)-imidazo[1,5-a]pyrimidine-8-carboxylic acid

HRID 418169ノート

反応式

HRID 418169 の反応式
C([O:3][C:4]([C:6]1[N:7]=[CH:8][N:9]2[C:14]([C:15]([F:18])([F:17])[F:16])=[CH:13][C:12]([C:19]3[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=3)=[N:11][C:10]=12)=[O:5])C.[OH-].[K+].O>C(O)(=O)C>[F:17][C:15]([F:16])([F:18])[C:14]1[N:9]2[CH:8]=[N:7][C:6]([C:4]([OH:5])=[O:3])=[C:10]2[N:11]=[C:12]([C:19]2[CH:20]=[CH:21][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:23][CH:24]=2)[CH:13]=1

参加物

5

反応物 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 866080034-Trifluoromethyl-2-(4-trifluoromethyl-phenyl)-imidazo[1,5-a]pyrimidine-8-carboxylic acid ethyl ester

生成物 1

HCID 866080044-Trifluoromethyl-2-(4-trifluoromethyl-phenyl)-imidazo[1,5-a]pyrimidine-8-carboxylic acid収率 37%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

A mixture of 4-trifluoromethyl-2-(4-trifluoromethyl-phenyl)-imidazo[1,5-a]pyrimidine-8-carboxylic acid ethyl ester (5.6 g, 13.9 mmol), 2M potassium hydroxide solution (111 ml) and water (55 ml) was stirred at room temperature for 5 h, cooled (ice-water), and acetic acid (30 ml) was added. The mixture was evaporated, acetic acid (150 ml) was added and the stirred solution was heated under reflux conditions for 20 min. The reaction mixture was evaporated, water (150 ml) was added followed by extraction with ethyl acetate (2×300 ml). The combined organic layers were washed with brine (2×150 ml), dried (MgSO4) and evaporated. The crude product was further purified by column chromatography on silica gel (ethyl acetate/heptane 1:1) to yield 4-trifluoromethyl-2-(4-trifluoromethyl-phenyl)-imidazo[1,5-a]pyrimidine-8-carboxylic acid (1.93 g, 37%) as a yellow solid. MS (ISN) 374.3 [(M−H)−]; mp 231° C.

後処理

  1. additionwas added
  2. customThe mixture was evaporated
  3. additionacetic acid (150 ml) was added
  4. temperaturethe stirred solution was heated under reflux conditions for 20 min
  5. customThe reaction mixture was evaporated
  6. additionwater (150 ml) was added
  7. extractionfollowed by extraction with ethyl acetate (2×300 ml)
  8. washThe combined organic layers were washed with brine (2×150 ml)
  9. dry with materialdried (MgSO4)
  10. customevaporated
  11. customThe crude product was further purified by column chromatography on silica gel (ethyl acetate/heptane 1:1)

出典と根拠

ORDレコード
ord-526bf539a62c4a00850187bce71cad73
出典データセット
uspto-grants-2012_01
特許番号
US08093263B2

反応ノート

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