1-Methylimidazole → 2,3'-Anhydrothymidine

HRID 2108148Notes

Reaction equation

HRID 2108148 reaction equation
[C@@H:1]1([N:9]2[CH:17]=[C:15]([CH3:16])[C:13](=[O:14])[NH:12][C:10]2=[O:11])[O:8][C@H:5]([CH2:6][OH:7])[C@@H:3](O)[CH2:2]1.S(OC1C=CC=CC=1)(OC1C=CC=CC=1)=O.CN1C=CN=C1>CN(C)C(=O)C>[CH3:16][C:15]1[C:13](=[O:14])[N:12]=[C:10]2[N:9]([C@@H:1]3[O:8][C@H:5]([CH2:6][OH:7])[C@@H:3]([O:11]2)[CH2:2]3)[CH:17]=1

Participants

5

Reactant 3

HCID 13901-MethylimidazoleHCID 5789ThymidineHCID 11390667diphenyl sulfite

Product 1

HCID 69157522,3'-AnhydrothymidineYield 65%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

For example, when thymidine is heated at ca 156° C. for 45 minutes with a four fold excess of diphenyl sulphite (see, for example, Gerrard, W., J. Chem. Soc., 218, (1940)) in the presence of a catalytic amount of N-methylimidazole in N,N-dimethylacetamide solution, and is then worked-up under basic conditions. 2,3'-anhydrothymidine may easily be isolated in almost 65% yield.

Sources & evidence

ORD record
ord-7921a2ef8ad443e483afa3824a4ee820
Source dataset
uspto-grants-1990_06
Patent number
US04937329

Reaction notes

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