Water → HCID 22662805, compound

HRID 392336Notes

Reaction equation

HRID 392336 reaction equation
F[C:2]1[C:3]([C:9]([O:11][CH3:12])=[O:10])=[N:4][C:5]([F:8])=[CH:6][N:7]=1.C([O-])(=[O:15])C.[Na+].C(OCC)(=O)C.O>CN(C)C=O>[F:8][C:5]1[N:4]=[C:3]([C:9]([O:11][CH3:12])=[O:10])[C:2](=[O:15])[NH:7][CH:6]=1

Participants

6

Conditions

Temperature
50 °C

Procedure

In 3.0 mL of N,N-dimethylformamide was dissolved 0.3 g of methyl 3,6-difluoro-2-pyrazinecarboxylate. After adding 0.16 g of sodium acetate at an ice-cooled temperature, the mixture thus obtained was stirred at 50° C. for 2.5 hours. The reaction mixture was poured into a mixture of 50 mL of ethyl acetate and 30 mL of water, and the organic layer was separated. The remaining aqueous phase was extracted with three 25 mL portions of ethyl acetate. The organic layers were united, washed successively with 15 mL of water and 15 ml of saturated aqueous solution of sodium chloride and dried on anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was purified by silica gel chromatography [eluent: n-hexane:ethyl acetate=1:2] to obtain 0.03 g of methyl 6-fluoro-3-oxo-3,4-dihydro-2-pyrazinecarboxylate as a colorless solid product.

Workup

  1. temperaturecooled temperature
  2. customthe mixture thus obtained
  3. customthe organic layer was separated
  4. extractionThe remaining aqueous phase was extracted with three 25 mL portions of ethyl acetate
  5. washwashed successively with 15 mL of water and 15 ml of saturated aqueous solution of sodium chloride
  6. dry with materialdried on anhydrous magnesium sulfate
  7. customthe solvent was removed under reduced pressure
  8. customThe residue was purified by silica gel chromatography [eluent: n-hexane:ethyl acetate=1:2]

Sources & evidence

ORD record
ord-8eb53c467a664280856e749befe08541
Source dataset
uspto-grants-2004_10
Patent number
US06800629B2

Reaction notes

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