Aminopyrimidines and Derivatives. 22¹. Synthesis of 3-Glycopyrano-Syl-vic-Triazolo [4,5-d]Pyrimidines, 7-Glycopyranosyl-Pyrrolo [2,3-d]PY-Rimidines and 4-Glycopyranosylamino-Furo [2,3-d]Pyrimidines²

Abstract

Reaction between 4-β-D-(O-acetyl)glycopyranosylaminopyrimidines 1 and chloracetylchloride yields the corresponding 5-α-chloracetyl derivatives 2, the hydrolysis products 3 and the corresponding 5-α-chloracetyl derivative of compounds 3. The former compounds were cyclized to the corresponding 7- β-D-glycopyranosyl-pyrrolo[2,3-d]pyrimidines 5 (2a yields 5,6-dihydro-4-β-D-(2,3,4,6-tetra-O-acetyl)glucopy-ranosylamino-2-methoxy-5-oxo-furo[2,3-d]pyrimidine 6a); the second ones to 3-β-D-(O-acetyl)glycopyranosyl-vic-triazolo[4,5-d] pyrimidines 10, and the last one to 4-β-D-(O-acetyl)glycopyranosylamino-furo[2,3-d] pyrimidines 7. The anticancer activity of some of these products is noticed.