Water → HCID 19365486, compound

HRID 849933Notes

Reaction equation

HRID 849933 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9](=[O:18])[NH:10][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:12][N:13]=2)=[C:4]([F:19])[CH:3]=1.[C:20](=O)([O-])[O-].[K+].[K+].CI.O>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9](=[O:18])[N:10]([CH3:20])[C:11]([C:14]([F:17])([F:15])[F:16])=[CH:12][N:13]=2)=[C:4]([F:19])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 19365499HCID 19365499, compound2×

Product 1

HCID 19365486HCID 19365486, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

First, 2.93 g of 3-(4-chloro-2-fluorophenyl)-6-trifluoromethyl-2-oxo-1,2-dihydropyrazine (compound 1-1005) was dissolved in 15 ml of N,N-dimethylformamide, to which 2.07 g of potassium carbonate and 1.25 ml of methyl iodide were added, and the mixture was stirred at 100° C. for 2 days. After completion of the reaction, the reaction mixture 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=6:1), which afforded 1.98 g (yield, 65%) of 3-(4-chloro-2-fluorophenyl)-1-methyl-6-trifluoromethyl-2-oxo-1,2-dihydropyrazine (present compound 1-11; m.p., 83.2° C.).

Workup

  1. additionwere added
  2. customAfter completion of the reaction
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with saturated sodium chloride solution
  5. dry with materialdried with anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-157d1d9adb9d407d882bd4dd5dbc7534
Source dataset
uspto-grants-2000_01
Patent number
US06015774

Reaction notes

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