Abstract
The reaction between 4, 6-dichloro-5-nitropyrimidine or 4-amino-5-nitro-6-chloropyrimidine and 2, 3, 4, 6-tetra-O-acetyl-D-glucopyranosylamine was investigated. In the former case, in addition to 4-chloro-5-nitro-6-(2, 3, 4, 6-tetra-O-acetylglucosylamino) pyrimidine, 4, 6-bis-glucosylamino derivative was obtained. Ring-closure of 4-chloro-5-amino-6-(2, 3, 4, 6 tetra-O-acetylglucosylamino) pyrimidine was achieved by acetic anhyd. ethyl orthoformate and further two step reaction afforded 9-β-D-glucopyranosyladenine. By the carbon disulfide ring-closure of 4, 5-diamino-6-(2, 3, 4, 6-tetra-O-acetylglucosylamino) pyrimidine, 9-β-D-glucosyladenine and N6-glucosyladenine was obtained in the ratio of 2 : 9. After deacetylation of triaminopyrimidine derivative, however, the reaction occurred in the reversed ratio of 9 : 4.