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

HRID 1293746ノート

反応式

HRID 1293746 の反応式
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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

反応条件

温度
60 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-daf1aa91a0ba44859f2d17489fc2331e
出典データセット
uspto-grants-2007_07
特許番号
US07238808B2

反応ノート

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