Water → 1-(4-Fluoro-phenyl)-2-pyrimidin-4-YL-ethanone

HRID 42565

반응식

HRID 42565 반응식
[H-].[Na+].[CH3:3][C:4]1[CH:9]=[CH:8][N:7]=[CH:6][N:5]=1.[F:10][C:11]1[CH:21]=[CH:20][C:14]([C:15](OCC)=[O:16])=[CH:13][CH:12]=1.O>CN(C=O)C.CCCCCC.CCOC(C)=O>[F:10][C:11]1[CH:21]=[CH:20][C:14]([C:15](=[O:16])[CH2:3][C:4]2[CH:9]=[CH:8][N:7]=[CH:6][N:5]=2)=[CH:13][CH:12]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 189224-MethylpyrimidineHCID 24758Sodium hydrideHCID 67976Benzoic acid, 4-fluoro-, ethyl ester

생성물 1

HCID 117360541-(4-Fluoro-phenyl)-2-pyrimidin-4-YL-ethanone수율 48%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 21226206Ethyl acetate hexane용매

반응 조건

온도
0 °C

실험 절차

To a suspension of NaH (2.26 g 50%, 47.7 mmol) in DMF (92 mL) under argon atmosphere and cooled to 0° C., 4-methylpyrimidine (3.00 g, 31.9 mmol) was added slowly. Then, ethyl 4-fluorobenzoate (6.40 g, 38.2 mmol) was added and it was stirred at room temperature overnight. Water was added and the solvent was evaporated. The residue was taken up in a mixture of EtOAc and brine. The phases were separated and the aqueous phase was reextracted with EtOAc. The combined organic phases were dried over Na2SO4 and concentrated to dryness. The crude product obtained by chromatography on silica gel using hexane-EtOAc mixtures of increasing polarity as eluent, to afford 3.30 g of the desired compound (yield: 48%).

후처리

  1. customthe solvent was evaporated
  2. additionThe residue was taken up in a mixture of EtOAc and brine
  3. customThe phases were separated
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. concentrationconcentrated to dryness
  6. customThe crude product obtained by chromatography on silica gel
  7. temperatureof increasing polarity as eluent

출처 및 근거

ORD 기록
ord-bf80a29417b249f9b43aef481339526f
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536194B2

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