Sulfuric Acid → 4-Difluoromethyl-2-(4-trifluoromethyl-phenyl)-imidazo[1,5-a]pyrimidine-8-carboxylic acid

HRID 269074노트

반응식

HRID 269074 반응식
C([O:3][C:4]([C:6]1[N:7]=[CH:8][N:9]2[C:14]([CH:15]([F:17])[F:16])=[CH:13][C:12]([C:18]3[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=3)=[N:11][C:10]=12)=[O:5])C.[OH-].[K+].S(=O)(=O)(O)O>O.CO>[F:17][CH:15]([F:16])[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:18]2[CH:19]=[CH:20][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:22][CH:23]=2)[CH:13]=1

참가 물질

6

반응물 3

HCID 1118Sulfuric AcidHCID 14797Potassium HydroxideHCID 670008454-Difluoromethyl-2-(4-trifluoromethyl-phenyl)-imidazo[1,5-a]pyrimidine-8-carboxylic acid ethyl ester

생성물 1

HCID 670010314-Difluoromethyl-2-(4-trifluoromethyl-phenyl)-imidazo[1,5-a]pyrimidine-8-carboxylic acid수율 39%

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

반응 조건

온도
60 °C

실험 절차

A mixture of 4-difluoromethyl-2-(4-trifluoromethyl-phenyl)-imidazo[1,5-a]pyrimidine-8-carboxylic acid ethyl ester (6.0 g, 15.6 mmol), potassium hydroxide 14 g (0.25 mmol) in water (62.5 ml) and methanol (125 ml) was stirred at room temperature for 2 h and at 60° C. for 1 h, cooled (ice-water), and 3N sulfuric acid (90 ml) was added. The formed precipitate (4.32 g) was collected by filtration, acetic acid (65 ml) was added and the stirred solution was heated under reflux conditions for 1 h. The reaction mixture was evaporated, ethyl acetate (30 ml) was added and the mixture was stirred for 30 min at 0° C. The precipitate was collected by filtration and dried to yield 4-difluoromethyl-2-(4-trifluoromethyl-phenyl)-imidazo[1,5-a]pyrimidine-8-carboxylic acid (2.15 g, 39%) as a yellow solid. MS (ISN) 356.0 [(M−H)−]; mp 238° C.

후처리

  1. additionwas added
  2. filtrationThe formed precipitate (4.32 g) was collected by filtration, acetic acid (65 ml)
  3. additionwas added
  4. temperaturethe stirred solution was heated under reflux conditions for 1 h
  5. customThe reaction mixture was evaporated
  6. additionethyl acetate (30 ml) was added
  7. stirringthe mixture was stirred for 30 min at 0° C
  8. filtrationThe precipitate was collected by filtration
  9. customdried

출처 및 근거

ORD 기록
ord-e422fc86bb6a4e388a806c3532a2afcd
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07446113B2

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