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

HRID 1242394노트

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HRID 1242394 반응식
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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 80711,2-Dimethoxyethane용매

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온도
80 °C

실험 절차

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)benzeneboronic 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 reaction 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 was obtained as greenish solid.

후처리

  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

출처 및 근거

ORD 기록
ord-99754bf21f5e4ce3af9e1dffca2f61e6
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07115611B2

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