Uridine → Cladribine

HRID 905529Notes

Reaction equation

[CH2:1]1[C@H:5](N2C(=O)NC(=O)C=C2)[O:4][C@H:3]([CH2:14][OH:15])[C@H:2]1[OH:16].[Cl:17][C:18]1[N:26]=[C:25]2[C:21]([NH:22][CH:23]=[N:24]2)=[C:20]([NH2:27])[N:19]=1.[C@@H]1(N2C=CC(=O)NC2=O)O[C@H](CO)[C@@H](O)[C@H]1O>>[CH:23]1[N:24]([C@@H:5]2[O:4][C@H:3]([CH2:14][OH:15])[C@@H:2]([OH:16])[CH2:1]2)[C:25]2[C:21](=[C:20]([NH2:27])[N:19]=[C:18]([Cl:17])[N:26]=2)[N:22]=1

Participants

Reactant 3

HCID 6029Uridine

HCID 13712Deoxyuridine

HCID 949042-Chloroadenine

Product 1

HCID 20279Cladribine

Procedure

reaction of 2-deoxyuridine with 2-chloroadenine, in the presence of uridine phosphorylase (UPase) and purine nucleoside phosphorylase (PNPase) in an aqueous reaction medium possibly containing up to 40% v/v of an aprotic dipolar solvent, to obtain cladribine dissolved in said reaction medium; b) isolation of the cladribine by precipitation by means of concentration and alkalinisation of the reaction medium up to a pH of 11.5-12.5.

Sources & evidence

ORD record: ord-059e8a4a45e941a1a89bcfb1b62a7be6
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08012717B2

Reaction notes

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