5-Fluorouracil → 3-Benzoyl-5-fluoropyrimidine-2,4(1H,3H)-dione

HRID 371913Notes

Reaction equation

HRID 371913 reaction equation
[F:1][C:2]1[C:3](=[O:9])[NH:4][C:5](=[O:8])[NH:6][CH:7]=1.[C:10](Cl)(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>N1C=CC=CC=1.O1CCOCC1>[C:10]([N:4]1[C:3](=[O:9])[C:2]([F:1])=[CH:7][NH:6][C:5]1=[O:8])(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 33855-FluorouracilHCID 7412Benzoyl chloride

Product 1

HCID 126908273-Benzoyl-5-fluoropyrimidine-2,4(1H,3H)-dioneYield 32%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 312751,4-DioxaneSolvent

Procedure

2.6 g (0.02 mole) of 5-fluorouracil was suspended in 10 ml of absolute pyridine and 10 ml of absolute dioxane, and the suspension was warmed to 80° C and stirred. 5.6 g (0.04 mole) of benzoyl chloride was then added dropwise thereto followed by stirring at 80° C for 1.5 hours to allow the mixture to react. After completion of the reaction, the reaction mixture was poured into ice-water followed by stirring, and the thus precipitated solid was filtered, washed with water and then dissolved in benzene while hot (80° C). Any insoluble matter was removed by filtration, and the filtrate allowed to cool to precipitate crystals, which were recovered by filtration to obtain 1.5 g of 3-N-benzoyl-5-fluorouracil in a yield of 32% (the filtrate was set aside). Melting Point: 170° C.

Workup

  1. stirringby stirring at 80° C for 1.5 hours
  2. customto react
  3. customAfter completion of the reaction
  4. stirringby stirring
  5. filtrationthe thus precipitated solid was filtered
  6. washwashed with water
  7. dissolutiondissolved in benzene while hot (80° C)
  8. customAny insoluble matter was removed by filtration
  9. temperatureto cool
  10. customto precipitate crystals, which
  11. filtrationwere recovered by filtration

Sources & evidence

ORD record
ord-9197ed243b7b4729b6952044f0c2c95e
Source dataset
uspto-grants-1978_05
Patent number
US04088646

Reaction notes

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