Uridine → Ribavirin

HRID 1720212Notes

Reaction equation

[NH:1]1[CH:5]=[N:4][C:3]([C:6]([NH2:8])=[O:7])=[N:2]1.N1C=CN=N1.[C@@H:14]1(N2C=CC(=O)NC2=O)[O:22][C@H:19]([CH2:20][OH:21])[C@@H:17]([OH:18])[C@H:15]1[OH:16].[C@@H]1(N2C3N=CN=C(O)C=3N=C2)O[C@H](CO)[C@@H](O)[C@H]1O.[C@@H]1(N2C=CC(N)=NC2=O)O[C@H](CO)[C@@H](O)[C@H]1O.[C@@H]1(N2C3N=CN=C(N)C=3N=C2)O[C@H](CO)[C@@H](O)[C@H]1O.[C@@H]1(N2C3N=C(N)NC(=O)C=3N=C2)O[C@H](CO)[C@@H](O)[C@H]1O.P([O-])(O)(O)=O.[K+]>>[CH:5]1[N:1]([C@@H:14]2[O:22][C@H:19]([CH2:20][OH:21])[C@@H:17]([OH:18])[C@H:15]2[OH:16])[N:2]=[C:3]([C:6]([NH2:8])=[O:7])[N:4]=1

Participants

Reactant 8

HCID 6029Uridine

HCID 6175Cytidine

HCID 60961Adenosine

HCID 516951Monobasic potassium phosphate

HCID 135398635Guanosine

HCID 178418936HCID 178418936, compound

HCID 178513825HCID 178513825, compound

HCID 178521066(2R,3S,4R,5R)-2-(hydroxymethyl)-5-(6-hydroxypurin-9-yl)oxolane-3,4-diol

Product 1

HCID 37542Ribavirin

Procedure

By using a substrate solution (pH 6.0) containing 40 mM 1,2,4-triazole-3-carboxamide (hereinafter called "triazole") as the base donor, 40 mM uridine, inosine, cytidine, adenosine or guanosine as the saccharide residue donor and 40 mM potassium dihydrogenphosphate, ribavirin was produced in the same manner as in Example 1. The results are shown in Table 7.

Sources & evidence

ORD record: ord-f7a0a6fa3b9d403a99372ff151c01923
Source dataset: uspto-grants-1996_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05506122

Reaction notes

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