Uridine → 2'-O-Methyluridine

HRID 488531Notes

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].[N+](=[CH2:20])=[N-]>>[CH3:20][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

Reactant 2

HCID 6029Uridine

HCID 9550Diazomethane

Product 1

HCID 1022122'-O-MethyluridineYield 58%

Procedure

Robins et al., 1974 J. Org. Chem. 39, 1891, describe the treatment of a methanolic solution of uridine with diazomethane (in glyme) in the presence of stannous chloride dihydrate (in methanol) to synthesize 2′-O-methyluridine (58% yield). This reaction also yielded a significant fraction (28%) of 3′-O-methyluridine which is purified away from the 2′-O-methyl form by chromatography.

Sources & evidence

ORD record: ord-cde5e500c3d84e1fb905b0a99f7691cd
Source dataset: uspto-grants-2005_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06972330B2

Reaction notes

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