Water → HCID 22662812, compound

HRID 392360Notes

Reaction equation

HRID 392360 reaction equation
F[C:2]1[C:3]([C:9]#[N:10])=[N:4][C:5]([F:8])=[CH:6][N:7]=1.C[O-].[Na+].[C:14](OCC)(=[O:16])C.O>CO>[F:8][C:5]1[N:4]=[C:3]([C:9]#[N:10])[C:2]([O:16][CH3:14])=[N:7][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 10942334Sodium MethoxideHCID 226628293,6-Difluoropyrazine-2-carbonitrile

Product 1

HCID 22662812HCID 22662812, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 25 mL of methanol was dissolved 2.5 g of 3,6-difluoro-2-pyrazinecarbonitrile. Then, 2.4 g of 28% methanolic solution of sodium methoxide was dropwise added at 5-15° C., and the mixture thus formed was stirred at an ice-cooled temperature for 2 hours. The reaction mixture was poured into a mixture of 50 mL of ethyl acetate and 50 mL of water, and the organic layer was separated. The organic layer thus obtained was washed successively with water and saturated aqueous solution of sodium chloride and dried on anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [eluent: n-hexane:ethyl acetate=10:1] to obtain 0.45 g of 6-fluoro-3-methoxy-2-pyrazinecarbonitrile as a colorless oily product.

Workup

  1. customthe mixture thus formed
  2. temperaturecooled temperature for 2 hours
  3. customthe organic layer was separated
  4. customThe organic layer thus obtained
  5. washwas washed successively with water and 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 thus obtained
  9. customwas purified by silica gel column chromatography [eluent: n-hexane:ethyl acetate=10:1]

Sources & evidence

ORD record
ord-5b2ea11154f34eb1b73a5a2cc85b447a
Source dataset
uspto-grants-2004_10
Patent number
US06800629B2

Reaction notes

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