Hydrochloric Acid → Methyl (4-methoxy-6-methylpyrimidin-2-yl)carbamate

Participants

Reaction Steps

2-Amino-4-methoxy-6-methylpyrimidine (50 g) was added portion wise to 50% sodium hydride (42.8 g) in 1 L dry THF. After stirring for 1/2 hour, dimethyl carbonate (58.5 g) was added dropwise with cooling. The mixture was stirred under nitrogen for ~16 hours at ambient temperature. Concentrated HCl (80 ml) was added slowly and using external cooling a pot temperature of ~25° C. was maintained. Saturated aqueous NaCl (80 ml) was then added. The solvents were decanted from the precipitated solids and dried over Na2SO4. Filtering and evaporating the solvents afforded the crude material which was recrystallized from hexane. 54 g m.p. 89-92.5° C. The infrared spectrum showed characteristic absorption bonds at 3400 and 1760 cm-1.

Provenance & Evidence