Uridine → HCID 178420746, compound

HRID 868497Notes

Reaction equation

HRID 868497 reaction equation
Cl[C:2]1[C:7]2[N:8]=[CH:9][NH:10][C:6]=2[N:5]=[CH:4][CH:3]=1.[C@@H]1(N2C=CC(=O)NC2=O)O[C@H](CO)[C@@H](O)[C@H]1O>P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[N:8]1[C:7]2[C:6](=[N:5][CH:4]=[CH:3][CH:2]=2)[NH:10][CH:9]=1

Participants

4

Reactant 2

HCID 6029Uridine2×HCID 178478247HCID 178478247, compound

Product 1

HCID 178420746HCID 178420746, compound

Reagents, catalysts & solvents 1

HCID 62657Potassium Phosphate, TribasicSolvent

Procedure

7-Chloro-3H-imidazo[4,5]pyridine (0.013 mole, 2 g) and uridine (0.014 mole, 3.4 g), were suspended in 32.3 ml of 0.01M potassium phosphate, pH 7.4. The enzyme catalysts purine nucleoside phosphorylase (970 units) and uridine phosphorylase (150 units) were added and the suspension mixed for two days at 37° C. The reaction was filtered and the filtrate lyophilized. The cake was extracted three times with acetone. These filtrates were combined and solvent removed in vacuo. The lyophilized powder was twice extracted with acetone and once extracted with methanol. These filtrates were combined with the extractions with methanol. These filtrates were combined with the extractions from above and solvent removed under vacuum. This powder was dissolved in 150 ml 30% n-PrOH/water (v/v) and chromatographed on a (7.5×90) cm column containing P-2 resin. Fractions containing product were pooled, dried in vacuo, resulting in 1.4 g of analytically pure 7-chloro-3-β-D-ribofuranosyl)-3H-imidazo[4,5-b]pyridine which had an Rf value of 0.25 on cellulose developed in (NH4)2SO4 :1M NaOAc:i-PrOH (79:19:2). M.p. 198° C.; UV λmax nm (ε×10-3) at pH 1 281, 284, 250; at pH 13, 279, 257; NMR (Me2SO-d6)δ 8.80 (s, 1H, H2), 8.34 (d, 1H, J=5.27, H5), 7.49 (d, 1H, J=5.26, H6), 6.07 (d, 1H, J=5.58, H1'), 4.5 (b, 1H, H2'), 4.1 (b, 1H, H3'), 4.0 (b, 1H, H4'), 3.5 (b, 2H, H5').

Workup

  1. additionthe suspension mixed for two days at 37° C
  2. filtrationThe reaction was filtered
  3. extractionThe cake was extracted three times with acetone
  4. customsolvent removed in vacuo
  5. extractionThe lyophilized powder was twice extracted with acetone
  6. extractiononce extracted with methanol
  7. extractionThese filtrates were combined with the extractions with methanol
  8. extractionThese filtrates were combined with the extractions from above and solvent
  9. customremoved under vacuum
  10. dissolutionThis powder was dissolved in 150 ml 30% n-PrOH/water (v/v)
  11. customchromatographed on a (7.5×90) cm column
  12. additioncontaining P-2 resin
  13. additionFractions containing product
  14. customdried in vacuo

Sources & evidence

ORD record
ord-863a064eea4a452894d427a1baca2a94
Source dataset
uspto-grants-1988_10
Patent number
US04780452

Reaction notes

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