Dimethyl Sulfoxide → 1-(4-Chlorobutyl)-3,5-dimethylpyrimidine-2,4(1H,3H)-dione

HRID 1678086Notes

Reaction equation

HRID 1678086 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[CH:11]=[C:10]([CH3:12])[C:9](=[O:13])[NH:8][C:7]1=[O:14].[OH-].[K+].O.[CH3:18]S(C)=O>>[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[CH:11]=[C:10]([CH3:12])[C:9](=[O:13])[N:8]([CH3:18])[C:7]1=[O:14]

Participants

5

Reactant 4

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 14797Potassium HydroxideHCID 593375871-(4-chlorobutyl)-5-methylpyrimidine-2,4(1H,3H)-dione

Product 1

HCID 673737481-(4-Chlorobutyl)-3,5-dimethylpyrimidine-2,4(1H,3H)-dione

Procedure

2.31 mmol (0.50 g) of 1-(4-chlorobutyl)-5-methylpyrimidine-2,4(1H,3H)-dione, 0.65 g (11.54 mmol) of KOH and 1.64 g (11.54 mmol) of methyl rodide in 20.5 ml of dimethyl sulfoxide (DMSO) were stirred at room temperature for 5 hours. Water was added to the reaction mixture, and the aqueous mixture was extracted three times with methyl tert-butyl ether. The combined organic phase was then washed three times with saturated aqueous brine, and the organic phase was dried, filtered to remove the desiccant and concentrated. 0.53 g of a pale cloudy oil was obtained.

Workup

  1. extractionthe aqueous mixture was extracted three times with methyl tert-butyl ether
  2. washThe combined organic phase was then washed three times with saturated aqueous brine
  3. customthe organic phase was dried
  4. filtrationfiltered
  5. customto remove the desiccant and
  6. concentrationconcentrated
  7. custom0.53 g of a pale cloudy oil was obtained

Sources & evidence

ORD record
ord-5b6e02836a65401fa8fc1371d1a0fae5
Source dataset
uspto-grants-2011_08
Patent number
US08008488B2

Reaction notes

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