Dimethylformamide → 5-Bromo-2-(2,2-diethoxyethoxy)pyrimidine

HRID 15063

Reaktionsgleichung

Reaktionsgleichung von HRID 15063
[CH2:1]([O:3][CH:4]([O:7][CH2:8][CH3:9])[CH2:5][OH:6])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].CN(C=O)C.[Br:21][C:22]1[CH:23]=[N:24][C:25](Cl)=[N:26][CH:27]=1>O>[Br:21][C:22]1[CH:23]=[N:24][C:25]([O:6][CH2:5][CH:4]([O:7][CH2:8][CH3:9])[O:3][CH2:1][CH3:2])=[N:26][CH:27]=1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 121292,2-DiethoxyethanolHCID 6066655-Bromo-2-chloropyrimidine

Produkt 1

HCID 684312375-Bromo-2-(2,2-diethoxyethoxy)pyrimidineAusbeute 94,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

2,2-Diethoxyethanol (1.6 g) and cesium carbonate (5.8 g) were added to DMF solution (10 mL) of 5-bromo-2-chloropyrimidine (1.15 g), and stirred at room temperature for 12 hours. After addition of water, the reaction liquid was extracted with ethyl acetate and dried over anhydrous magnesium sulfate. Concentrating the solvent under reduced pressure, the residue was purified on silica gel column chromatography (C-200; ethyl acetate:hexane=1:9-1:4) to provide the title compound (1.63 g, 94%).

Aufarbeitung

  1. customthe reaction liquid
  2. extractionwas extracted with ethyl acetate
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationConcentrating the solvent under reduced pressure
  5. customthe residue was purified on silica gel column chromatography (C-200; ethyl acetate:hexane=1:9-1:4)

Quellen und Nachweise

ORD-Eintrag
ord-1ba2013ec1264fe3af9606dd2c8fb343
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732456B2

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