5-Fluorouracil → Tegafur

HRID 1413195Notes

Reaction equation

HRID 1413195 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 97.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
70 °C

Procedure

In an autoclave, 520 g of 5-fluorouracil, 1400 g of 2,3-dihydrofuran and 1.56 l of pyridine were heated together at 185° C. for 3 hours. After cooling, the reaction mixture was concentrated to dryness under reduced pressure and the residue was dissolved in 6 l of ethanol-water(1:1). The solution was heated at 70° C. for 2 hours, after which it was treated with activated charcoal. After filtration, the solution was concentrated under reduced pressure to about one-half of its original volume. After cooling, the resultant crystals were recovered by filtration and dried. By the above procedure was obtained 780 g of 1-(tetrahydro-2-furyl)-5-fluorouracil. If necessary, this product may be recrystallized from ethanol. Recrystallization yielded 600 g of colorless needles, melting point: 167.5° C.

Workup

  1. temperatureAfter cooling
  2. concentrationthe reaction mixture was concentrated to dryness under reduced pressure
  3. dissolutionthe residue was dissolved in 6 l of ethanol-water(1:1)
  4. additionafter which it was treated with activated charcoal
  5. filtrationAfter filtration
  6. concentrationthe solution was concentrated under reduced pressure to about one-half of its original volume
  7. temperatureAfter cooling
  8. filtrationthe resultant crystals were recovered by filtration
  9. customdried

Sources & evidence

ORD record
ord-bc46a1fa5ee14ce0842e794972aa7692
Source dataset
uspto-grants-1981_02
Patent number
US04249006

Reaction notes

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