Uridine → 7-Anilino-3-(5-deoxy-beta-D-ribofuranosyl)-3H-imidazo[4,5-b]pyridine

Reaction equation

[NH:1]([C:8]1[CH:13]=[CH:12][N:11]=[C:10]2[NH:14][CH:15]=[N:16][C:9]=12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C@@H:17]1(N2C=CC(=O)NC2=O)[O:24][C@H:22]([CH3:23])[C@@H:20]([OH:21])[C@H:18]1[OH:19].[N-]=[N+]=[N-].[K+].[C@@H]1(N2C=CC(=O)NC2=O)O[C@H](CO)[C@@H](O)[C@H]1O>>[NH:1]([C:8]1[CH:13]=[CH:12][N:11]=[C:10]2[N:14]([C@@H:17]3[O:24][C@H:22]([CH3:23])[C@@H:20]([OH:21])[C@H:18]3[OH:19])[CH:15]=[N:16][C:9]=12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 4

HCID 6029Uridine

HCID 4444375'-Deoxyuridine

HCID 10290740Potassium azide

HCID 178420476HCID 178420476, compound

Product 1

HCID 541440467-Anilino-3-(5-deoxy-beta-D-ribofuranosyl)-3H-imidazo[4,5-b]pyridineYield 77%

Procedure

7-Anilino-3H-imidazo[4,5-b]pyridine (0.8 g, 3.77 mmol) and 5'-deoxyuridine (2 g, 0.87 mmol) were added to a 10 mL solution of 10 mM KxHxPO4, pH 7.4 and 0.04% potassium azide. After mixing, 180 units of uridine phosphorylase and 1800 units of purine nucleoside phosphorylase were added. The reaction was continuously mixed at 35° C. for 6 days. Solids were collected by filtration and recrystallized from boiling ethanol yielding 0.943 g of the 7-anilino-3-(5-deoxy-β-D-ribofuranosyl)-3H-imidazo[4,5-b]pyridine. This corresponded to a yield of 77%; m.p. 219° C.