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

HRID 868495Notes

Reaction equation

HRID 868495 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.[Cl:17][CH2:18][C@H:19]1[O:23][C@@H:22](N2C=CC(=O)NC2=O)[C@H:21]([OH:32])[C@@H:20]1[OH:33]>>[NH:1]([C:8]1[CH:13]=[CH:12][N:11]=[C:10]2[N:14]([C@@H:22]3[O:23][C@H:19]([CH2:18][Cl:17])[C@@H:20]([OH:33])[C@H:21]3[OH:32])[CH:15]=[N:16][C:9]=12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 113115665'-Chloro-5'-deoxy-uridineHCID 178420476HCID 178420476, compound

Product 1

HCID 143917757-anilino-3-(5-chloro-5-deoxy-beta-D-ribofuranosyl)-3H-imidazo[4,5-b]pyridine

Conditions

Temperature
35 °C

Procedure

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.):

Workup

  1. customUridine phosphorylase (315 units) and purine nucleoside phosphorylase (1800 units) previously purified from E
  2. additioncoli, were added
  3. additionAfter 4 days an additional 84 units of uridine phosphorylase and 100 mL phosphate buffer were added
  4. filtrationTwenty-one days later the particulates were collected by filtration
  5. customrecrystallized

Sources & evidence

ORD record
ord-0993bd377f1c451083eb8d0f91e40e3c
Source dataset
uspto-grants-1988_10
Patent number
US04780452

Reaction notes

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