5-Fluorouracil → Tegafur

HRID 127692Notes

Reaction equation

HRID 127692 reaction equation
[F:1][C:2]1[C:3](=[O:9])[NH:4][C:5](=[O:8])[NH:6][CH:7]=1.Cl.C(N(CC)CC)C.[O:18]1[CH:22]=[CH:21][CH2:20][CH2:19]1>CN(C)C=O>[O:18]1[CH2:22][CH2:21][CH2:20][CH:19]1[N:6]1[CH:7]=[C:2]([F:1])[C:3](=[O:9])[NH:4][C:5]1=[O:8]

Participants

5

Reactant 3

HCID 33855-FluorouracilHCID 11130Triethylamine hydrochlorideHCID 709342,3-Dihydrofuran

Product 1

HCID 5386Tegafur

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

In 15 ml of dimethylformamide were dissolved 1.3 g of 5-fluorouracil and 0.41 g of triethylamine hydrochloride. To this solution were added 3 ml of 2,3-dihydrofuran and the mixture was reacted in an autoclave for 16 hours at 150° C. After the reaction, dimethylformamide was removed from the reaction liquid by distillation and the residue was treated in the same manner as described in Example 7 to obtain 0.8 g of 1-(2-tetrahydrofuryl)-5-fluorouracil. From the chloroform insoluble matter 0.6 g of the starting 5-fluorouracil was recovered. The yield of the end product was 74% based on the consumed 5-fluorouracil.

Workup

  1. customthe mixture was reacted in an autoclave for 16 hours at 150° C
  2. customwas removed from the reaction liquid by distillation
  3. additionthe residue was treated in the same manner

Sources & evidence

ORD record
ord-b1afd9df20d24dd3b2dad69e2b37af88
Source dataset
uspto-grants-1981_03
Patent number
US04256885

Reaction notes

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