5-Fluorouracil → Tegafur

HRID 127701Notes

Reaction equation

HRID 127701 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-Fluorouracil2×HCID 709342,3-Dihydrofuran

Product 1

HCID 5386TegafurYield 71.5%

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 acid clay and the mixture was reacted at 130° C. for 10 hours. The reaction liquid was treated in the same manner as described in Example 21 whereby 1.65 g of 5-fluorouracil were recovered and 14.30 g of 1-(2-tetrahydrofuryl)-5-fluorouracil were obtained. The yield of the end product was 81.9% based on the consumed 5-fluorouracil.

Workup

  1. customthe mixture was reacted at 130° C. for 10 hours
  2. customThe reaction liquid
  3. additionwas treated in the same manner
  4. customwere recovered

Sources & evidence

ORD record
ord-41329383c6b44aea8581b5bfc82a2fbf
Source dataset
uspto-grants-1981_03
Patent number
US04256885

Reaction notes

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