Uridine → 2'-O-Methyluridine

HRID 264732Notes

Reaction equation

HRID 264732 reaction equation
[C@@H:1]1([N:10]2[CH:17]=[CH:16][C:14](=[O:15])[NH:13][C:11]2=[O:12])[O:9][C@H:6]([CH2:7][OH:8])[C@@H:4]([OH:5])[C@H:2]1[OH:3].[CH2:18]([Sn](=O)CCCC)CCC.C([C@@]1(O)[C@H](OCCCC)[C@@H](C(=[SnH2])O)O[C@H]1N1C=CC(=O)NC1=O)CCC.IC>>[CH3:18][O:3][C@@H:2]1[C@H:4]([OH:5])[C@@H:6]([CH2:7][OH:8])[O:9][C@H:1]1[N:10]1[CH:17]=[CH:16][C:14](=[O:15])[NH:13][C:11]1=[O:12]

Participants

5

Reactant 4

HCID 6029UridineHCID 6328Methyl iodideHCID 61221Dibutyltin oxideHCID 1317200902',3'-O-dibutylstannyleneuridine

Product 1

HCID 1022122'-O-Methyluridine

Procedure

As per the procedure of Example 49, uridine (8.5 g) was treated with dibutyl tin oxide (8.2 g, 1 eq). The resulting 2',3'-O-dibutylstannylene uridine was treated with iodomethane (16 ml) at 42° C. as per Example 50 to give a mixture of the 2' and 3' alkylated products (3.5 g) as a foam.

Workup

  1. customto give

Sources & evidence

ORD record
ord-94e61d78ff324933b9742f2a6cae9bf5
Source dataset
uspto-grants-1997_07
Patent number
US05646265

Reaction notes

Loading…