Water → 4-(3-Fluorophenyl)-6-(2-butynyloxy)pyrimidine

HRID 1592125Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1592125
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=2)[N:5]=[CH:4][N:3]=1.[CH2:15]([OH:19])[C:16]#[C:17][CH3:18].[H-].[Na+].O>CN(C)C=O>[F:14][C:10]1[CH:9]=[C:8]([C:6]2[CH:7]=[C:2]([O:19][CH2:15][C:16]#[C:17][CH3:18])[N:3]=[CH:4][N:5]=2)[CH:13]=[CH:12][CH:11]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 129912-Butyn-1-olHCID 24758Sodium hydrideHCID 6103714-Chloro-6-(3-fluorophenyl)pyrimidine

Produkt 1

HCID 225997204-(3-Fluorophenyl)-6-(2-butynyloxy)pyrimidineAusbeute 63,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

In 7 ml of N,N-dimethylformamide were dissolved 204 mg of 4-chloro-6-(3-fluorophenyl)pyrimidine and 82 mg of 2-butyn-1-ol, to which 47 mg of sodium hydride (60% in oil) was added, followed by stirring at room temperature for 6 hours. The reaction mixture was then poured into water and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated. The resulting residue was subjected to silica gel column chromatography to give 151 mg of 4-(3-fluorophenyl)-6-(2-butynyloxy)pyrimidine (the present compound (57)).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-3a1cf85021cb46caa6827ae61ab039d4
Quelldatensatz
uspto-grants-2007_11
Patentnummer
US07291730B2

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