Uridine → 5,7-Dichloro-3-beta-D-ribofuranosyl-3H-imidazo[4,5-b]pyridine

HRID 868499Notes

Reaction equation

HRID 868499 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]2[NH:8][CH:9]=[N:10][C:5]2=[C:4]([Cl:11])[CH:3]=1.[C@@H:12]1(N2C=CC(=O)NC2=O)[O:20][C@H:17]([CH2:18][OH:19])[C@@H:15]([OH:16])[C@H:13]1[OH:14].[N-]=[N+]=[N-].[K+]>P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cl:1][C:2]1[N:7]=[C:6]2[N:8]([C@@H:12]3[O:20][C@H:17]([CH2:18][OH:19])[C@@H:15]([OH:16])[C@H:13]3[OH:14])[CH:9]=[N:10][C:5]2=[C:4]([Cl:11])[CH:3]=1

Participants

5

Reactant 3

HCID 6029Uridine2×HCID 10290740Potassium azideHCID 1784781755,7-dichloro-4H-imidazo[4,5-b]pyridine

Product 1

HCID 140582465,7-Dichloro-3-beta-D-ribofuranosyl-3H-imidazo[4,5-b]pyridine

Reagents, catalysts & solvents 1

HCID 62657Potassium Phosphate, TribasicSolvent

Procedure

5,7-Dichloro-3H-imidazo[4,5-b]pyridine (0.0053 mole, 1.0 g) and uridine (0.00795 mole, 1.94 g), were suspended in 20 ml potassium phosphate, 0.01M at pH 7 with 0.04% potassium azide. The catalysts, purine nucleoside phosphorylase (1900 units) and uridine phosphorylase (1300 units) were added and the suspension mixed for 10 days at 35° C. The reaction was filtered and the cake dissolved in boiling methanol. After filtering, the volume was doubled with water then reduced to one quarter the volume in vacuo at 40° C. The resulting precipitate was collected by filtration and contained 1.3 g (0.0037 mole) of analytically pure 5,7-Dichloro-3-β-D-ribofuranosyl-3H-imidazo[4,5-b]pyridine. M.p. 156°-158° C.; UV λmax nm (ε×10-3) at pH 1, 10% EtOH, 187(8.2), 256(4.2); at pH 13, 10% EtOH, 289(8.7 ), 260(5.0); [α]D20 =-15.6, (C=0.5, DMF); NMR (MC2SO-d6) δ 8.85 (s, 1H, H2), 7.68 (s, 1H, H6), 5.99 (d, 1H, J=5.49, H1'), 5.0 (m, 1H, H2'), 4.5 (m, 1H, H3'), 4.0 (m, 1H, H4'), 3.5 (b, 1H, H5')

Workup

  1. additionthe suspension mixed for 10 days at 35° C
  2. filtrationThe reaction was filtered
  3. dissolutionthe cake dissolved
  4. filtrationAfter filtering
  5. customat 40° C
  6. filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-b6a4472a043b4910a0cc00b972a406d0
Source dataset
uspto-grants-1988_10
Patent number
US04780452

Reaction notes

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