Ammonia → HCID 13377365, compound

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Reaction Steps

To 25 ml of methanol saturated with ammonia gas was added with stirring 1.00 g (4.35 mmole) of 5,7-dichloro-3-(n-propyl)imidazo[1,5-c]pyrimidine (from Example 36). Stirring was continued at 20° C. for 1.5 hours, at which time the mixture was poured into 50 ml of water and extracted with four 35 ml portions of chloroform. The combined extracts were washed twice with 50 ml portions of water, once with 35 ml of saturated aqueous sodium chloride solution and dried over magnesium sulfate. Concentration provided a residue which was triturated with diethyl ether to provide a yellow solid which was mostly 5-amino-7-chloro-3-(n-propyl)imidazo[1,5-c]pyrimidine. The ether solution was evaporated to provide a yellow solid. The solid was dissolved in cyclohexane, treated with decolorizing charcoal and cooled. The small amount of precipitate formed was 5-amino-7-chloro-3-(n-propyl)imidazo[1,5-c]pyrimidine. Evaporation of the cyclohexane gave yellow solid 7-chloro-5-methoxy-3-(n-propyl)imidazo[1,5-c]pyrimidine, m.p. 76°- 77° C. Analysis: Calculated for C10H12ClN3O: %C, 53.2; %H, 5.4; %N, 18.6; Found; %C, 52.9; %H, 5.4; %N, 18.1.

Provenance & Evidence