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

HRID 1413194

Reaktionsgleichung

Reaktionsgleichung von HRID 1413194
[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>C1C=CC=CC=1>[O:10]1[CH2:11][CH2:12][CH2:13][CH:14]1[N:6]1[CH:7]=[C:2]([F:1])[C:3](=[O:9])[N:4]([CH:11]2[CH2:12][CH2:13][CH2:14][O:10]2)[C:5]1=[O:8]

Komponenten

4

Edukt 2

HCID 33855-FluorouracilHCID 709342,3-Dihydrofuran

Produkt 1

HCID 1249561,3-Bis(tetrahydro-2-furanyl)-5-fluoro-2,4-pyrimidinedioneAusbeute 48,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

In a closed tubular reactor, 1.3 g of 5-fluorouracil, 5 ml of benzene and 14 g of 2,3-dihydrofuran were heated together at 200° C. for 6 hours. After cooling, the reaction mixture was concentrated to dryness under reduced pressure and the residue was separated and purified by column chromatography on 25 g silica gel. From the chloroform eluate, the fractions rich in the contemplated compound were collected. The solvent was distilled off and the residue was recrystallized from petroleum ether. By the above procedure was obtained 1.3 g of 1,3-bis-(tetrahydro-2-furyl)-5-fluorouracil.

Aufarbeitung

  1. temperatureAfter cooling
  2. concentrationthe reaction mixture was concentrated to dryness under reduced pressure
  3. customthe residue was separated
  4. custompurified by column chromatography on 25 g silica gel
  5. customFrom the chloroform eluate, the fractions rich in the contemplated compound were collected
  6. distillationThe solvent was distilled off
  7. customthe residue was recrystallized from petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-115974711b3944299d4af57f79afd416
Quelldatensatz
uspto-grants-1981_02
Patentnummer
US04249006

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