5-Fluorouracil → Tegafur

HRID 127700Notes

Reaction equation

HRID 127700 reaction equation
[F:1][C:2]1[C:3](=[O:9])[NH:4][C:5](=[O:8])[NH:6][CH:7]=1.[O:10]1[CH:14]=[CH:13][CH2:12][CH2:11]1>N1C=CC=CC=1>[O:10]1[CH2:14][CH2:13][CH2:12][CH:11]1[N:6]1[CH:7]=[C:2]([F:1])[C:3](=[O:9])[NH:4][C:5]1=[O:8]

Participants

4

Reactant 2

HCID 33855-FluorouracilHCID 709342,3-Dihydrofuran

Product 1

HCID 5386TegafurYield 67.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In 100 ml of pyridine were dissolved 13.0 g of 5-fluorouracil and 10.5 g of 2,3-dihydrofuran. To the solution were added 7.5 g of alumina and the mixture was reacted at 130° C. for 24 hours. After completion of the reaction, the reaction liquid was filtered to remove the catalyst and the solvent was distilled off. The residue was dissolved in chloroform to recover 3.04 g of insoluble unreacted 5-fluorouracil. The chloroform was distilled off from the chloroform layer and the residue was recrystallized from ethanol to give 13.52 g of 1-(2-tetrahydrofuryl)-5-fluorouracil. The yield of the end product was 88.9% based on the consumed 5-fluorouracil.

Workup

  1. additionTo the solution were added 7.5 g of alumina
  2. customthe mixture was reacted at 130° C. for 24 hours
  3. customAfter completion of the reaction
  4. customthe reaction liquid
  5. filtrationwas filtered
  6. customto remove the catalyst
  7. distillationthe solvent was distilled off
  8. dissolutionThe residue was dissolved in chloroform
  9. customto recover 3.04 g of insoluble unreacted 5-fluorouracil
  10. distillationThe chloroform was distilled off from the chloroform layer
  11. customthe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-c1e4b8686e14418f9dd602393db02f58
Source dataset
uspto-grants-1981_03
Patent number
US04256885

Reaction notes

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