N,N-Dimethyl-1,3-propanediamine → 4-(1,3-diethyl-2,3,6,7-tetrahydro-2,6-dioxo-1H-purin-8-yl)-N-[3-(dimethylamino)-propyl]benzenesulfonamide monohydrochloride

Participants

Reaction Steps

A mixture of 4-(1,3-diethyl-2,3,6,7-tetrahydro-2,6,-dioxo-1H-purin-8-yl)benzenesulfonic acid, (5.0 g, 0.014 moles) and N,N-dimethylformamide (150 ml) is cooled to 0° and treated with thionyl chloride (3.3 g, 0.027 moles). When the addition is complete, the reaction mixture is permitted to warm to ambient temperature and stirred vigorously until a thick slurry is formed. To this slurry is added 3-(dimethylamino)propylamine (14 g, 0.137 moles) in one portion, the mixture is stirred until a clear solution is obtained, and concentrated on a rotary evaporator. The residue is taken up in water, filtered, recrystallized from ethanol, and dried at 78° to yield 1.53 grams of 4-(1,3-diethyl-2,3,6,7-tetrahydro-2,6-dioxo-1H-purin-8-yl)-N-[3-(dimethylamino)-propyl]benzenesulfonamide monohydrochloride, mp 291°-292° C.(d).

Provenance & Evidence