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

HRID 42565

反応式

HRID 42565 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 21226206Ethyl acetate hexane溶媒

反応条件

温度
0 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-bf80a29417b249f9b43aef481339526f
出典データセット
uspto-grants-2013_09
特許番号
US08536194B2

関連ノート

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