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

HRID 42565

Reaktionsgleichung

Reaktionsgleichung von HRID 42565
[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

Komponenten

7

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 21226206Ethyl acetate hexaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

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%).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-bf80a29417b249f9b43aef481339526f
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536194B2

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