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

HRID 1678076Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1678076
[OH:1][C:2]1[C:7]([CH3:8])=[CH:6][N:5]=[CH:4][N:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:16][CH2:17][CH2:18][CH2:19][Cl:20].[OH2:21]>CS(C)=O>[Cl:20][CH2:19][CH2:18][CH2:17][CH2:16][N:5]1[CH:6]=[C:7]([CH3:8])[C:2]([OH:1])=[N:3][C:4]1=[O:21]

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 813641-Bromo-4-chlorobutaneHCID 178430618HCID 178430618, Verbindung

Produkt 1

HCID 593375871-(4-chlorobutyl)-5-methylpyrimidine-2,4(1H,3H)-dione

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 stirred at room temperature for 5 hours. Water was added to the reaction mixture, which 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 1-(4-chlorobutyl)-4-hydroxy-5-methylpyrimidin-2(1H)-one.

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
  5. customresulted in 7.1 g of 1-(4-chlorobutyl)-4-hydroxy-5-methylpyrimidin-2(1H)-one

Quellen und Nachweise

ORD-Eintrag
ord-f4ab46d7c72d4da993a4f1166da2c4de
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US08008488B2

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