Ethyl Acetate → Methyl 3-amino-6-fluoropyrazine-2-carboxylate

Participants

Reaction Steps

In 10 mL of acetic acid was dissolved 0.5 g of methyl 3-amino-2-pyrazinecarboxylate. At room temperature, 10% fluorine gas (a fluorine gas diluted with nitrogen gas) was introduced into the solution at a rate of 23 mL per minute for a period of 32 minutes. After stirring the solution for 30 minutes at room temperature, the reaction mixture was added to a mixture of 50 mL of saturated aqueous solution of sodium hydrogen carbonate and 50 mL of ethyl acetate, and the organic layer was separated. The organic layer thus obtained was washed successively with 10 mL of water and 10 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 column chromatography [eluent: n-hexane:ethyl acetate=3:1] to obtain 0.01 g of methyl 3-amino-6-fluoro-2-pyrazinecarboxylate as a light yellow-colored solid product.

Provenance & Evidence