Dimethyl Sulfate → HCID 19889037, compound

HRID 653581Notes

Reaction equation

HRID 653581 reaction equation
[H-].[Na+].[Cl:3][C:4]1[C:9]([C:10]2[O:11][C:12]([CH3:15])=[N:13][N:14]=2)=[CH:8][C:7]([N:16]2[C:21](=[O:22])[CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[NH:18][C:17]2=[O:27])=[C:6]([F:28])[CH:5]=1.[H][H].[CH3:31]OS(=O)(=O)OC>CN(C)C=O>[Cl:3][C:4]1[C:9]([C:10]2[O:11][C:12]([CH3:15])=[N:13][N:14]=2)=[CH:8][C:7]([N:16]2[C:21](=[O:22])[CH:20]=[C:19]([C:23]([F:24])([F:25])[F:26])[N:18]([CH3:31])[C:17]2=[O:27])=[C:6]([F:28])[CH:5]=1

Participants

6

Reactant 4

HCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 19889042HCID 19889042, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19889037HCID 19889037, compoundYield 30.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 0.31 g of sodium hydride (oil, purity: 55%) in 13 ml of dimethylformamide, a solution of 2.5 g of 3-(4-chloro-2-fluoro-5-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl)-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione in 20 ml of N,N-dimethylformamide was added dropwise at 25° C. After evolution of hydrogen ceased, 1.02 g of dimethylsulfuric acid was added over a period of 15 minutes. The mixed solution was stirred at room temperature for 2 hours and extracted with ethyl acetate by adding water. The extract was dried over anhydrous sodium sulfate. Then the solvent was distilled off and the residue was purified by preparative high performance liquid chromatography using acetonitrile/water (5:1) as eluent to obtain 0.78 g of the objective compound.

Workup

  1. extractionextracted with ethyl acetate
  2. additionby adding water
  3. dry with materialThe extract was dried over anhydrous sodium sulfate
  4. distillationThen the solvent was distilled off
  5. customthe residue was purified by preparative high performance liquid chromatography

Sources & evidence

ORD record
ord-0ce8867f9f9848a090dd4c13cec59a9f
Source dataset
uspto-grants-1992_07
Patent number
US05127935

Reaction notes

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