Water → 3-(4-chloro-6-fluoro-3-methoxy-2-nitrophenyl)-1-methyl-6-trifluoromethyl-2,4(1H, 3H)-pyrimidinedione

HRID 1271728Notes

Reaction equation

HRID 1271728 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N:9]2[C:14](=[O:15])[CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[NH:11][C:10]2=[O:20])=[C:4]([N+:21]([O-:23])=[O:22])[C:3]=1[O:24][CH3:25].[C:26](=O)([O-])[O-].[K+].[K+].COS(OC)(=O)=O.O>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N:9]2[C:14](=[O:15])[CH:13]=[C:12]([C:16]([F:18])([F:17])[F:19])[N:11]([CH3:26])[C:10]2=[O:20])=[C:4]([N+:21]([O-:23])=[O:22])[C:3]=1[O:24][CH3:25]

Participants

6

Reactant 4

HCID 962WaterHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 865858983-(4Chloro-6-fluoro-3-methoxy-2-nitrophenyl)-6-trifluoromethyl-2,4(1H, 3H)-pyrimidinedione

Product 1

HCID 541638193-(4-chloro-6-fluoro-3-methoxy-2-nitrophenyl)-1-methyl-6-trifluoromethyl-2,4(1H, 3H)-pyrimidinedioneYield 83.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(4Chloro-6-fluoro-3-methoxy-2-nitrophenyl)-6trifluoromethyl-2,4(1H, 3H)-pyrimidinedione (9 g, 23.5 mmol) was dissolved in dimethylformamide (90 ml) and to this were added potassium carbonate (3.9 g, 28.2 mmol) and dimethylsulfate (10.2 g, 47 mmol) with stirring. The solution was stirred at ambient temperature for 12 hr and water was added. Product was extracted in ethyl acetate and the organic layer was washed with water and dried over anhydrous sodium sulfate. Removal of the solvent afforded a crude product which was purified by column chromatography on silica gel. Elution of the column with methylene chloride afforded the title compound (7.8 g).

Workup

  1. stirringThe solution was stirred at ambient temperature for 12 hr
  2. extractionProduct was extracted in ethyl acetate
  3. washthe organic layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customRemoval of the solvent
  6. customafforded a crude product which
  7. customwas purified by column chromatography on silica gel
  8. washElution of the column with methylene chloride

Sources & evidence

ORD record
ord-56825903f6ea4209873db903512900d9
Source dataset
uspto-grants-2007_04
Patent number
USRE039590E1

Reaction notes

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