Uridine → HCID 14391767, compound

HRID 868493Notes

Reaction equation

HRID 868493 reaction equation
[C@@H:1]1(N2C=CC(=O)NC2=O)[O:9][C@H:6]([CH2:7][OH:8])[C@@H:4]([OH:5])[C@H:2]1[OH:3].[NH:18]([C:25]1[CH:30]=[CH:29][N:28]=[C:27]2[NH:31][CH:32]=[N:33][C:26]=12)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[OH-].[K+]>>[NH:18]([C:25]1[CH:30]=[CH:29][N:28]=[C:27]2[N:31]([C@@H:1]3[O:9][C@H:6]([CH2:7][OH:8])[C@@H:4]([OH:5])[C@H:2]3[OH:3])[CH:32]=[N:33][C:26]=12)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 3

HCID 6029UridineHCID 14797Potassium HydroxideHCID 178420476HCID 178420476, compound

Product 1

HCID 14391767HCID 14391767, compoundYield 91%

Procedure

Uridine (50 mmoles, 12.3 g) and 7-anilino-3H-imidazo[4,5-b]pyridine (33 mmole, 7.0 g), were suspended in 65 mL of 7.6 mM KxHxPO4, pH 8.0. After stirring, the pH of this suspension was adjusted from pH 6.6 to 7.4 with potassium hydroxide. The enzyme catalysts purified from Escherichia coli, purine nucleoside phosphorylase (13,000 I.U.) and uridine phosphorylase (335 I.U.) (Krenitsky et al., Biochemistry, 20, 3615, 1981 and U.S. Pat. No. 4,381,344) were then added and the suspension stirred at 38° C. for 5 days. The reaction mixture was filtered. The solids were washed with water and suspended in 250 mL of methanol, brought to a boil, and filtered while hot. The filtrate was dried and extracted with water at room temperature. The product in the washed solids was further purified by several recrystallizations from boiling water. Analytically pure 7-anilino-3-β-D-ribofuranosyl-3H-imidazo[4,5-b]pyridine (30 mmole, 10.46 g), m.p. 189° C. was obtained representing a yield of 91% with respect to the amount of 7-anilino-3H-imidazo[4,5-b]pyridine base used.

Workup

  1. customThe enzyme catalysts purified from Escherichia coli, purine nucleoside phosphorylase (13,000 I.U.) and uridine phosphorylase (335 I.U.) (Krenitsky et al., Biochemistry, 20, 3615, 1981 and U.S
  2. addition4,381,344) were then added
  3. stirringthe suspension stirred at 38° C. for 5 days
  4. filtrationThe reaction mixture was filtered
  5. washThe solids were washed with water
  6. filtrationfiltered while hot
  7. customThe filtrate was dried
  8. extractionextracted with water at room temperature
  9. customThe product in the washed solids was further purified by several recrystallizations

Sources & evidence

ORD record
ord-4243d9e0d2fc402fb51eaddc00abbe5e
Source dataset
uspto-grants-1988_10
Patent number
US04780452

Reaction notes

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