6-Chloropurine riboside → N-[2-(2,5-dihydro-1H-pyrrol-1-yl) ethyl]adenosine, monohydrochloride

Participants

Reaction Steps

To a suspension of 6 chloropurine riboside (1.27 g, 4.42 mmol) in 10 ml of absolute ethanol was added 2-(2,5-dihydro-1H-pyrrol-1-yl)-1-ethanamine (prepared in accordance with Arzneim. Forsch. 21 (12) 2089 (1971)) in an amount of 0.54 g (4.9 mmol). The reaction mixture was heated under reflux for 40 hours. Concentration of the reaction mixture in vacuo gave a residue which was chromatographed on cellulose powder (Whatman CC 31). The eluent was 85 parts n-butanol and 15 parts water. Fraction monitoring was accomplished by thin layer chromatography on silica gel (Kieselgel 60 F254) eluting with a mixture of 20 parts methanol, 79 parts methylene chloride and one part ammonium hydroxide. The chromatography gave a glass which was azeotroped with water 3 times to remove the n butanol. Lyophilization of the aqueous solution gave the title compound in an amount of 0.41 g (21g yield) as a white powder (mp 88°-105° C.)

Provenance & Evidence