Sodium Methoxide → Methyl 4-amino-2-propylimidazol-5-carboxylate

Participants

Reaction Conditions

Reaction Steps

To stirred methanol at -2° C. was added sodium methoxide (108 g, 2.0 mol) in portions over a period of 40 minutes. To this clear solution at -3° C. was added a solution of methyl N-(N'-cyanobutyrimidoyl)glycinate (Example 3, 344 g, 1.9 mol) in methanol (600 mL) over a period of 30 minutes. The resulting orange solution was allowed to warm to 13° C. over a period of 1 hour, then refluxed for 1 hour. The dark solution was cooled to room temperature and evaporated to dryness under reduced pressure. The residue was partitioned between water and ethyl acetate. The aqueous layer was extracted with ethyl acetate (4×1 L) and the combined organic layers washed with a saturated aqueous solution of sodium chloride. The combined organic layers were dried over anhydrous magnesium sulfate, filtered, and the filtrate evaporated to dryness under reduced pressure. The residue was recrystallized from ethyl acetate at -10° C. to afford 131 g (38% yield) of methyl 4-amino-2-propylimidazol-5-carboxylate, mp 133°-136° C. MS (DEI) 184 (M+1).

Provenance & Evidence