5-Fluorouracil → 1,3-Bis(tetrahydro-2-furanyl)-5-fluoro-2,4-pyrimidinedione

HRID 1112267

Reaktionsgleichung

Reaktionsgleichung von HRID 1112267
[F:1][C:2]1[C:3](=[O:9])[NH:4][C:5](=[O:8])[NH:6][CH:7]=1.[Sb](Cl)(Cl)Cl.[O:14]1[CH:18]=[CH:17][CH2:16][CH2:15]1>N1C=CC=CC=1>[O:14]1[CH2:15][CH2:16][CH2:17][CH:18]1[N:6]1[CH:7]=[C:2]([F:1])[C:3](=[O:9])[N:4]([CH:15]2[CH2:16][CH2:17][CH2:18][O:14]2)[C:5]1=[O:8].[O:14]1[CH2:18][CH2:17][CH2:16][CH:15]1[N:6]1[CH:7]=[C:2]([F:1])[C:3](=[O:9])[NH:4][C:5]1=[O:8]

Komponenten

6

Edukt 3

HCID 33855-FluorouracilHCID 24814Antimony trichlorideHCID 709342,3-Dihydrofuran2×

Produkt 2

HCID 5386TegafurAusbeute 27 %HCID 1249561,3-Bis(tetrahydro-2-furanyl)-5-fluoro-2,4-pyrimidinedioneAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel2×

Versuchsvorschrift

In a sealed tube, 780 mg (6 m mole) of 5-fluorouracil, 5 ml of pyridine, 100 mg (0.44 m mole) of antimony trichloride and 1.26 g (18 m mole) of 2,3-dihydrofuran were heated at 100° C for 3 hours. The reaction mixture was further admixed with 800 mg (11.5 m mole) of 2,3-dihydrofuran and the mixture was heated for 17 hours. After the reaction, pyridine was distilled off under a reduced pressure and the residue was dissolved in chloroform and the insoluble matters were separated by a filtration. Chloroform was distilled off from the filtrate and the residue was purified by a column chromatography using a silica gel column (mixture of chloroform and acetone = 8 : 1 (V/V) as a developing medium) to obtain 1.10 g of N1,N3 -bis(2-tetrahydrofuryl)-5-fluorouracil (yield: 68.0%) and 325 mg of N1 -(2-tetrahydrofuryl)-5-fluorouracil (yield: 27%).

Aufarbeitung

  1. temperaturethe mixture was heated for 17 hours
  2. distillationwas distilled off under a reduced pressure
  3. dissolutionthe residue was dissolved in chloroform
  4. customthe insoluble matters were separated by a filtration
  5. distillationChloroform was distilled off from the filtrate
  6. customthe residue was purified by a column chromatography
  7. additionmixture of chloroform and acetone = 8 : 1 (V/V) as a developing medium)

Quellen und Nachweise

ORD-Eintrag
ord-ebfa396b349c40569fe000b0600d9a04
Quelldatensatz
uspto-grants-1978_10
Patentnummer
US04121037

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