5'-Chloro-5'-deoxy-uridine → 7-anilino-3-(5-chloro-5-deoxy-beta-D-ribofuranosyl)-3H-imidazo[4,5-b]pyridine

Participants

Reaction Conditions

Reaction Steps

7-Anilino-3H-imidazo[4,5-b]pyridine (0.8 g, 3.7 mmol) and 5'-chloro-5'-deoxyuridine (15 g, 5.7 mmol) were combined in 10 mL of 10 mM KxHxPO4, pH 7.4. Uridine phosphorylase (315 units) and purine nucleoside phosphorylase (1800 units) previously purified from E. coli, were added and the reaction stirred at 35° C. After 4 days an additional 84 units of uridine phosphorylase and 100 mL phosphate buffer were added. Twenty-one days later the particulates were collected by filtration and recrystallized from boiling ethanol yielding 0.982 g of 72% of 7-anilino-3-(5-chloro-5-deoxy-β-D-ribofuranosyl)-3H-imidazo[4,5-b]pyridine, m.p. 195° C. (dec.):

Provenance & Evidence