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

HRID 1413196

Reaction equation

HRID 1413196 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[CH2:11][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]

Participants

4

Reactant 2

HCID 33855-FluorouracilHCID 709342,3-Dihydrofuran

Product 1

HCID 1249561,3-Bis(tetrahydro-2-furanyl)-5-fluoro-2,4-pyrimidinedione

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
150 °C

Procedure

In 20.8 ml of pyridine were dissolved 5.2 g (40 m mol) of 5-fluorouracil and 14 g (200 m mol) of 2,3-dihydrofuran. The solution were heated at about 150° C. in a closed tubular reactor under agitation for 6 hours. After the reaction, the reaction mixture was concentrated to dryness under reduced pressure. The residue was dissolved in chloroform and the solution was passed through a column of silica gel. The column was eluated with chloroform and the effluent was concentrated to dryness under reduced pressure. The residue was washed with a small amount of petroleum ether to give the above-mentioned compound as colorless crystals.

Workup

  1. customAfter the reaction
  2. concentrationthe reaction mixture was concentrated to dryness under reduced pressure
  3. dissolutionThe residue was dissolved in chloroform
  4. concentrationthe effluent was concentrated to dryness under reduced pressure
  5. washThe residue was washed with a small amount of petroleum ether

Sources & evidence

ORD record
ord-2992a554a28e4ff7a9ce0121c7aa404d
Source dataset
uspto-grants-1981_02
Patent number
US04249006

Linked notes

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