Methyl iodide → HCID 19365515, compound

HRID 849921Notes

Reaction equation

HRID 849921 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10](=[O:19])[NH:11][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:13][N:14]=1.[C:20](=O)([O-])[O-].[K+].[K+].CI>CC(C)=O>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10]([O:19][CH3:20])=[N:11][C:12]([C:15]([F:16])([F:18])[F:17])=[CH:13][N:14]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 19365505HCID 19365505, compound2×

Product 1

HCID 19365515HCID 19365515, compoundYield 65.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

First, 23.3 g of 3-(2,4-difluorophenyl)-6-trifluoromethyl-2-oxo-1,2-dihydropyrazine (compound 1-1004) was dissolved in 150 ml of acetone, to which 17.5 g of potassium carbonate and 14.3 g of methyl iodide were added, and the mixture was stirred at room temperature for 15 hours. After completion of the reaction, most of the acetone was distilled out under reduced pressure, and the residue was poured into water, followed by extraction with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried with anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography (eluent, hexane/ethyl acetate=19:1), which afforded 16.1 g of 3-(2,4-difluorophenyl)-2-methoxy-6-trifluoromethylpyrazine (m.p., 55.3° C.) as the earlier eluted O-methylated compound and 7.13 g (yield, 29%) of 3-(2,4-difluorophenyl)-1-methyl-6-trifluoromethyl-2-oxo-1,2-dihydropyrazine (present compound 1-10; m.p., 73.0° C.) as the later eluted desired compound.

Workup

  1. additionwere added
  2. customAfter completion of the reaction
  3. distillationmost of the acetone was distilled out under reduced pressure
  4. additionthe residue was poured into water
  5. extractionfollowed by extraction with ethyl acetate
  6. washThe organic layer was washed with saturated sodium chloride solution
  7. dry with materialdried with anhydrous magnesium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-7221024be0ff493dbe638fce756b52b5
Source dataset
uspto-grants-2000_01
Patent number
US06015774

Reaction notes

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