Water → 6-(3,4-dimethoxyphenyl)-1,3-dimethyl-2,4(1H,3H)-pyrimidinedione

HRID 65147Notes

Reaction equation

HRID 65147 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[NH:16][C:15](=O)NC(=O)[CH:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[H-].[Na+].CI.[OH2:23].[CH3:24][N:25]([CH3:28])[CH:26]=[O:27]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[N:16]([CH3:15])[C:24](=[O:23])[N:25]([CH3:28])[C:26](=[O:27])[CH:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 212432066-(3,4-dimethoxyphenyl)-2,4(1H,3H)-pyrimidinedione

Product 1

HCID 140964656-(3,4-dimethoxyphenyl)-1,3-dimethyl-2,4(1H,3H)-pyrimidinedione

Conditions

Temperature
60 °C

Procedure

To a solution of 6-(3,4-dimethoxyphenyl)-2,4(1H,3H)-pyrimidinedione (8.0 g) in N,N-dimethylformamide (50 ml) and added sodium hydride (50% in oil, 3.40 g) and the mixture was heated at 60° C. for 30 minutes with stirring. To this mixture which was cooled to ambient temperature was added methyl iodide (40 ml) and the resulting mixture was stirred at the same temperature for 90 minutes. To the reaction mixture was added water and evaporated under reduced pressure. The residue was diluted with water (300 ml) and extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate and evaporated under reduced pressure. The residue was subjected to column chromatography on silica gel and eluted with a mixture of chloroform and methanol. The fractions containing the object compound were combined and concentrated under reduced pressure to give 6-(3,4-dimethoxyphenyl)-1,3-dimethyl-2,4(1H,3H)-pyrimidinedione (1.94 g).

Workup

  1. temperatureTo this mixture which was cooled to ambient temperature
  2. stirringthe resulting mixture was stirred at the same temperature for 90 minutes
  3. customevaporated under reduced pressure
  4. additionThe residue was diluted with water (300 ml)
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with water
  7. dry with materialdried over magnesium sulfate
  8. customevaporated under reduced pressure
  9. washeluted with a mixture of chloroform and methanol
  10. additionThe fractions containing the object compound
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5e51aece8ffa4d73ab931959e3722954
Source dataset
uspto-grants-1986_09
Patent number
US04612376

Reaction notes

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