5-Fluorouracil → Tegafur

HRID 127695Notes

Reaction equation

HRID 127695 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 5386Tegafur

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In 50 ml of pyridine were dissolved 2.5 g of 5-fluorouracil and 0.64 g of ferric chloride. The reaction was carried out at 120° C. for 8 hours while adding 2.3 ml of 2,3-dihydrofuran to the solution. The reaction liquid was treated in the same manner as described in Example 12 to obtain 1.8 g of 1-(2-tetrahydrofuryl)-5-fluorouracil. From the aqueous layer 0.8 g of unreacted 5-fluorouracil was recovered. The yield of the end product was 69% based on the consumed 5-fluorouracil.

Workup

  1. customThe reaction liquid
  2. additionwas treated in the same manner

Sources & evidence

ORD record
ord-891afac35d664956b703a0742fabe610
Source dataset
uspto-grants-1981_03
Patent number
US04256885

Reaction notes

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