5-Fluorouracil → Tegafur

HRID 127687Notes

Reaction equation

HRID 127687 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>CC(N(C)C)=O>[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 31374DimethylacetamideSolvent

Procedure

In 20 ml of dimethylacetamide were dissolved 1.3 g of 5-fluorouracil. To this solution were added 1.4 g of 2,3-dihydrofuran and the mixture was reacted in an autoclave for 5 hours at 180° C. After completion of the reaction, the reaction liquid was treated in the same manner as described in Example 1 whereby 0.22 g of the starting 5-fluorouracil was recovered as a substance insoluble in chloroform and 1.43 g of 1-(2-tetrahydrofuryl)-5-fluorouracil were obtained. The yield of the end product was 86.4% based on the consumed 5-fluorouracil.

Workup

  1. customthe mixture was reacted in an autoclave for 5 hours at 180° C
  2. customAfter completion of the reaction
  3. customthe reaction liquid
  4. additionwas treated in the same manner
  5. customwas recovered as a substance insoluble in chloroform

Sources & evidence

ORD record
ord-84dcf8def63446be81cd9632f2d10976
Source dataset
uspto-grants-1981_03
Patent number
US04256885

Reaction notes

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