Methanol → Methyl 3-amino-5-methoxypyrazine-2-carboxylate

Reaction equation

[H-].[Na+].[CH3:3][O:4][C:5]([C:7]1[C:12]([NH2:13])=[N:11][C:10](Cl)=[CH:9][N:8]=1)=[O:6].[NH4+].[Cl-].[CH3:17][OH:18]>>[CH3:3][O:4][C:5]([C:7]1[C:12]([NH2:13])=[N:11][C:10]([O:18][CH3:17])=[CH:9][N:8]=1)=[O:6]

Participants

Reactant 4

HCID 887Methanol

HCID 24758Sodium hydride

HCID 25517Ammonium Chloride

HCID 53417426Methyl 3-amino-5-chloropyrazine-2-carboxylate

Product 1

HCID 53438909Methyl 3-amino-5-methoxypyrazine-2-carboxylate

Procedure

At 0° C. 75 mg (1.866 mmol) 60% sodium hydride in oil was added in portions to 5 ml MeOH and the mixture was stirred at room temperature for 30 min. After re-cooling to 0° C. 350 mg (1.866 mmol) 3-amino-5-chloro-pyrazine-2-carboxylic acid methyl ester (GB 1248146) was added and the mixture was allowed to warm to room temperature and stirred over night. Saturated aqueous NH4Cl was added and the mixture was extracted with DCM and EtOAc, the combined organic layers were washed with saturated aqueous sodium chloride, dried with Na2SO4 and evaporated. The residue was purified by chromatography on silica gel (cyclohexane to EtOAc) to provide the title compound as colorless solid.