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Water → HCID 22247880, compound

HRID 392351
Notes
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Reaction equation

HRID 392351 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-].[Na+].[C:16](OCC)(=[O:18])C.O>CO>[F:8][C:5]1[N:4]=[C:3]([C:9]([O:11][CH3:12])=[O:10])[C:2]([O:18][CH3:16])=[N:7][CH:6]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 10942334Sodium MethoxideHCID 22662801Methyl 3,6-difluoropyrazine-2-carboxylate

Product 1

HCID 22247880HCID 22247880, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
0 °C

Procedure

In 4 mL of methanol was dissolved 0.2 g of methyl 3,6-difluoro-2-pyrazinecarboxylate. Then, a 28% methanol solution of sodium methoxide was added at −25° C., and the mixture thus obtained was stirred at 0° C. for 10 minutes. The reaction mixture was poured into a mixture of 30 mL of ethyl acetate and 30 mL of water, and the organic layer was separated. The organic layer thus obtained was 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 thus obtained was purified by silica gel chromatography [eluent: n-hexane:ethyl acetate=5:1] to obtain 0.09 g of methyl 6-fluoro-3-methoxy-2-pyrazinecarboxylate as a colorless solid product.

Workup

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

Sources & evidence

ORD record
ord-5cf10171da94486e8b63d5cc3f7f7f61
Source dataset
uspto-grants-2004_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06800629B2

Reaction notes

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