Methyl iodide → HCID 15544298, compound

HRID 653579Notes

Reaction equation

HRID 653579 reaction equation
[F:1][C:2]1[C:12]([N:13]2[C:18](=[O:19])[CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[NH:15][C:14]2=[O:24])=[CH:11][C:5]2[NH:6][C:7](=[O:10])[CH2:8][O:9][C:4]=2[CH:3]=1.[C:25](=O)([O-])[O-].[K+].[K+].CI>CN(C)C=O>[F:1][C:2]1[C:12]([N:13]2[C:18](=[O:19])[CH:17]=[C:16]([C:20]([F:21])([F:22])[F:23])[N:15]([CH3:25])[C:14]2=[O:24])=[CH:11][C:5]2[NH:6][C:7](=[O:10])[CH2:8][O:9][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 19889039HCID 19889039, compound

Product 1

HCID 15544298HCID 15544298, compoundYield 119.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.85 g of 3-(7-fluoro-3-oxo-2H-1,4-benzoxazin-6-yl)-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione was dissolved in 8.5 ml of N,N-dimethylformamide. Then 0.17 g of anhydrous potassium carbonate and 0.15 ml of methyl iodide were added and the mixed solution was stirred for 4 hours. After the reaction was completed, N,N-dimethylformamide was distilled off and the residue was extracted with ethyl acetate by adding water. The extract was washed with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then ethyl acetate was distilled off to obtain a crude product. This product was purified by column chromatography using chloroform as developing solvent to yield 0.53 g of the objective compound as pale yellow crystals.

Workup

  1. distillationN,N-dimethylformamide was distilled off
  2. extractionthe residue was extracted with ethyl acetate
  3. additionby adding water
  4. washThe extract was washed with a saturated sodium chloride aqueous solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationethyl acetate was distilled off
  7. customto obtain a crude product
  8. customThis product was purified by column chromatography

Sources & evidence

ORD record
ord-aa2ac3b6c2124a4f813bc073df8deb32
Source dataset
uspto-grants-1992_07
Patent number
US05127935

Reaction notes

Loading…