4,6-Dichloro-5-nitropyrimidine → HCID 178526808, compound

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Reaction Steps

A solution of 20 g. of 4,6-dichloro-5-nitropyrimidine was prepared in ether. An aqueous solution containing 14 g. of β-chloroethylamine hydrochloride and 24 g. of sodium bicarbonate were added thereto and the subsequent mixture agitated for about 30 minutes. The ether layer was separated, and the separated layer washed with water and dried. Removal of the ether in vacuo yielded an oil containing chiefly 4-(β-chloroethylamino)-5-nitro-6-chloropyrimidine plus a small quantity of 5-nitro-4,6-bis(β-chloroethyl)pyrimidine (the disubstituted product) and a very small quantity of starting material. The oily residue was allowed to stand in chloroform for about one day. A solid comprising 7-(β-chloroethylamino)-8-nitro-2,3-dihydroimidazo[1,2-c]pyrimidine hydrochloride precipitated and the precipitate was separated by filtration, 7-(β-chloroethyl)amino-8-nitro-2,3-dihydroimidazo[1,2-c]pyrimidine hydrochloride thus prepared decomposed at 135° C. after recrystallization from chloroform; yield=5.378 g.

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