Reaction #992711

ord-059e8a4a45e941a1a89bcfb1b62a7be6

Reaction equation

O=c1ccn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]1
2-deoxyuridine
Nc1nc(Cl)nc2nc[nH]c12
2-chloroadenine
O=c1ccn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c(=O)[nH]1
uridine
→
Nc1nc(Cl)nc2c1ncn2[C@H]1C[C@H](O)[C@@H](CO)O1
cladribine

Reactants

O=c1ccn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]1
2-deoxyuridine
Nc1nc(Cl)nc2nc[nH]c12
2-chloroadenine
O=c1ccn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c(=O)[nH]1
uridine
—
purine nucleoside

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

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.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08012717B2uspto-grants-2011_09