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

HRID 1678076Notes

Reaction equation

HRID 1678076 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-f4ab46d7c72d4da993a4f1166da2c4de
Source dataset
uspto-grants-2011_08
Patent number
US08008488B2

Reaction notes

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