Water → 1-(4-chlorobutyl)-5-methylpyrimidine-2,4(1H,3H)-dione

HRID 1640457

Reaktionsgleichung

Reaktionsgleichung von HRID 1640457
[OH:1][C:2]1[C:7]([CH3:8])=[CH:6][NH:5][C:4](=[O:9])[N:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:17][CH2:18][CH2:19][CH2:20][Cl:21].O>CS(C)=O>[Cl:21][CH2:20][CH2:19][CH2:18][CH2:17][N:5]1[CH:6]=[C:7]([CH3:8])[C:2](=[O:1])[NH:3][C:4]1=[O:9]

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 813641-Bromo-4-chlorobutaneHCID 178430899HCID 178430899, Verbindung

Produkt 1

HCID 593375871-(4-chlorobutyl)-5-methylpyrimidine-2,4(1H,3H)-dioneAusbeute 41 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

10.1 g (80.0 mmol) of 4-hydroxy-5-methylpyrimidin-2(1H)-one (thymine) in 300 ml of dimethyl sulfoxide (DMSO) and 11.1 g (80.0 mmol) of K2CO3 were stirred at room temperature for 1 hour. Then 13.7 g (80.0 mmol) of 1-bromo-4-chlorobutane were added dropwise to the mixture, and the reaction mixture was then stirred at room temperature for 5 hours. Water was added to the reaction mixture, and it was then extracted with ethyl acetate. The aqueous phase was then neutralized and extracted with methylene chloride. Drying of the organic phase, removal of the desiccant by filtration and evaporation of the solvent to dryness in vacuo resulted in 7.1 g of the title compound

Aufarbeitung

  1. extractionwas then extracted with ethyl acetate
  2. extractionextracted with methylene chloride
  3. customDrying of the organic phase, removal of the
  4. filtrationdesiccant by filtration and evaporation of the solvent to dryness in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-b162710974be453188102109c39d2459
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08114875B2

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