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

HRID 418169노트

반응식

HRID 418169 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-526bf539a62c4a00850187bce71cad73
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08093263B2

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