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

HRID 2376724Notes

Reaction equation

HRID 2376724 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
0 °C

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-f42833aa1689468d9b2209d0b9f8dae8
Source dataset
uspto-grants-2008_12
Patent number
US07468376B2

Reaction notes

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