5-Fluorouracil → 5-Fluoro-4-thiouracil

HRID 1075165Notes

Reaction equation

HRID 1075165 reaction equation
[F:1][C:2]1[C:3](=O)[NH:4][C:5](=[O:8])[NH:6][CH:7]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:11].O1CCOCC1>N1C=CC=CC=1>[F:1][C:2]1[C:3](=[S:11])[NH:4][C:5](=[O:8])[NH:6][CH:7]=1

Participants

5

Reactant 3

HCID 33855-FluorouracilHCID 14817Phosphorus sulfide (P2S5)HCID 312751,4-Dioxane

Product 1

HCID 27812135-Fluoro-4-thiouracilYield 80%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Prepared from 5-fluorouracil by the method of Ueda and Fox (see above) using phosphorus pentasulphide in pyridine. We find that dioxan is a better solvent in this reaction in which case the yield was 80% of a more pure product.

Workup

  1. customin this reaction in which case the yield was 80% of a more pure product

Sources & evidence

ORD record
ord-2a6589d625fe475292c6216055f43040
Source dataset
uspto-grants-1983_07
Patent number
US04395406

Reaction notes

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