Ethanol → 2-Methyl-5-(4-trifluoromethyl-phenyl)-pyrimidine

HRID 1726999ノート

反応式

HRID 1726999 の反応式
C(=O)([O-])[O-].[Na+].[Na+].Br[C:8]1[CH:9]=[N:10][C:11]([CH3:14])=[N:12][CH:13]=1.[F:15][C:16]([F:27])([F:26])[C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1.C(O)C>O.COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:14][C:11]1[N:10]=[CH:9][C:8]([C:20]2[CH:21]=[CH:22][C:17]([C:16]([F:27])([F:26])[F:15])=[CH:18][CH:19]=2)=[CH:13][N:12]=1

参加物

8

反応物 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 143877445-Bromo-2-methylpyrimidine

生成物 1

HCID 219359462-Methyl-5-(4-trifluoromethyl-phenyl)-pyrimidine収率 84%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
80 °C

実験手順

A solution of 7.95 g (75 mmol) of sodium carbonate in 15 ml of water was added to a mixture of 2.6 g (15 mmol) of 5-bromo-2-methylpyrimidine (Coll. Czech. Chem. Comm. 14 (1949), 223-235), of 4 g (21 mmol) of 4-(trifluoromethyl)benzene boronic acid and of 0.52 g (0.45 mmol) of tetrakis(triphenylphosphine)palladium in a mixture of 50 ml of 1,2-dimethoxy-ethane and of 30 ml of ethanol. The mixture was stirred at 80° C. for 2 hours, afterwards, it was concentrated by distilling off the major part of the organic solvents. Subsequently, the residue was extracted with 3 portions of tert.-butyl methyl ether. The combined organic phases were washed with water and brine, dried over anhydrous sodium sulfate and finally evaporated. The residue was chromatographed on silicagel with a mixture of dichloromethane/tert.-butyl methyl ether (9/1 vol./vol.) as eluent. 3 g of the title compound were obtained as greenish solid. MS: 239.2 (M+H)+.

後処理

  1. concentrationafterwards, it was concentrated
  2. distillationby distilling off the major part of the organic solvents
  3. extractionSubsequently, the residue was extracted with 3 portions of tert.-butyl methyl ether
  4. washThe combined organic phases were washed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customfinally evaporated
  7. customThe residue was chromatographed on silicagel with a mixture of dichloromethane/tert.-butyl methyl ether (9/1 vol./vol.) as eluent

出典と根拠

ORDレコード
ord-29c030a69b204ce4a0b9e655c2c11fac
出典データセット
uspto-grants-2009_02
特許番号
US07495001B2

反応ノート

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