Hydrochloric Acid → 6-Benzyloxy-1-methyl-2,5-dioxo-1,2,3,5-tetrahydroimidazo[1,2-a]pyrimidine-7-carboxylic acid

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Reaction Conditions

Reaction Steps

A solution of intermediate 12, ethyl 6-benzyloxy-1-methyl-2,5-dioxo-1,2,3,5-tetrahydroimidazo[1,2-a]pyrimidine-7-carboxylate, (0.084 g, 0.24 mmol) in a mixture of ethanol (5 ml) and tetrahydrofuran (5 ml) was treated with 1.0 ml of a 1 M aqueous sodium hydroxide and the resulting mixture was stirred at 25° C. for 30 min. The reaction mixture was then acidified with 1 N hydrochloric acid and extracted with ethyl acetate. The organic phase was washed with brine, dried over anhydrous magnesium sulfate and concentrated to give 0.073 g (95% yield) of the title acid as white crystals; mp 194° C. (ethyl acetate). 1HNMR 400 MHz (DMSO-d6) δ (ppm): 3.07 (3H, s, NCH3), 4.54 (2H, s, CH2), 5.04 (2H, s, CH2), 7.3–7.5 (5H, m, aromatics), 13.8 (1H, s, OH). MS (ESI+) m/z 316 [M+H+].

Provenance & Evidence