Ethyl Acetate → HCID 18670663, compound

Participants

Reaction Steps

To a solution of 1.0 g of methyl 5-amino-6-mercaptonicotinate in N,N-dimethylformamide (30 ml) were added 0.52 g of sodium hydride (oily: 60% or more) and 0.97 g of 2,3-dichloropyrazine and the resulting mixture was reacted at 100° C. for 2 hours. Then ethyl acetate was added to the reaction mixture, which was then washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. After distilling off the solvent under reduced pressure, diethyl ether was added to the residue and the crystals thus precipitated were taken up by filtration to thereby give 0.43 g of crude methyl 10H-pyrazino[2,3-b]pyrido[3,2-e][1,4]thiazin-8-carboxylate as a brown solid. To a solution of 1.43 g of these crude crystals in N,N-dimethylformamide (50 ml) were added 0.26 g of sodium hydride (60% oily) and 0.5 g of chloromethyl methyl ether and the resulting mixture was reacted under ice-cooling for 1 hour. After adding ethyl acetate, the mixture was washed with a saturated aqueous solution of sodium chloride. The organic layer was dried over anhydrous magnesium sulfate. After distilling off the solvent under reduced pressure, diethyl ether was added to the residue and the crystals thus precipitated were taken up by filtration to thereby give 1.5 g of the title compound as red crystals.

Provenance & Evidence