Water → 3,4-Dihydro-6-(3,4-dimethoxyphenyl)-2,3-dimethylpyrimidin-4-one

HRID 4322Notes

Reaction equation

HRID 4322 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[N:16]=[C:15]([CH3:17])[NH:14][C:13](=[O:18])[CH:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[CH3:19]C(C)([O-])C.[K+].CI.O>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[N:16]=[C:15]([CH3:17])[N:14]([CH3:19])[C:13](=[O:18])[CH:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 23665647Potassium tert-butoxideHCID 1357361743,4-Dihydro-6-(3,4-dimethoxyphenyl)-2-methylpyrimidin-4-one

Product 1

HCID 201523073,4-Dihydro-6-(3,4-dimethoxyphenyl)-2,3-dimethylpyrimidin-4-oneYield 65.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 3,4-dihydro-6-(3,4 dimethoxyphenyl)-2-methylpyrimidin-4-one (2.0 g) in N,N-dimethylformamide (20 ml) were added potassium tert.butoxide (1.08 g) and methyl iodide (1.0 ml), and stirred at ambient temperature for an hour. Resulting mixture was poured into water, and extracted with ethyl acetate. The organic layer was chromatographed on silica gel eluting with chloroform to give 3,4-dihydro-6-(3,4-dimethoxyphenyl)-2,3-dimethylpyrimidin-4-one (1.38 g).

Workup

  1. customResulting mixture
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was chromatographed on silica gel eluting with chloroform

Sources & evidence

ORD record
ord-6991b219f52b4e25941ed6cba7871dad
Source dataset
uspto-grants-1988_02
Patent number
US04725600

Reaction notes

Loading…