Hydrochloric Acid → Methyl 6-amino-3-methoxy-2-pyrazinecarboxylate

Participants

Reaction Conditions

Reaction Steps

In an atmosphere of nitrogen gas, 11.4 g of methyl 6-bromo-3-methoxy-2-pyrazinecarboxylate was dissolved in 227 mL of toluene, and 10.3 g of benzophenoneimine, 0.42 g of tris(dibenzylideneacetone)dipalladium, 0.86 g of (s)-(−)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl and 6.20 g of sodium tert-butoxide were successively added. The mixture thus obtained was stirred at 80° C. for one hour. After cooling the reaction mixture, it was filtered. The filtrate was purified by column chromatography [eluent: toluene:ethyl acetate=20:1]. The oily product thus obtained was dissolved in 140 mL of tetrahydrofuran, 7 mL of 2 mol/L hydrochloric acid was added, and the mixture thus obtained was stirred at room temperature for 15 minutes. A mixture of 200 mL of chloroform and 50 mL of water was added to the reaction mixture and then 1 mol/L sodium hydroxide was added to alkalinize the mixture, and the organic layer was separated. The organic layer thus obtained was washed with a 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 column chromatography [eluent: toluene:ethyl acetate=1:1] to obtain 3.64 g of methyl 6-amino-3-methoxy-2-pyrazinecarboxylate as a yellow-colored oily product.

Provenance & Evidence