5-Fluorouracil → 1(2H)-Pyrimidinecarboxamide, N-butyl-5-fluoro-3,4-dihydro-2,4-dioxo-

HRID 1834766Notes

Reaction equation

HRID 1834766 reaction equation
[F:1][C:2]1[C:3](=[O:9])[NH:4][C:5](=[O:8])[NH:6][CH:7]=1.[CH2:10]([N:14]=[C:15]=[O:16])[CH2:11][CH2:12][CH3:13]>CN(C)C=O>[CH2:10]([NH:14][C:15]([N:6]1[CH:7]=[C:2]([F:1])[C:3](=[O:9])[NH:4][C:5]1=[O:8])=[O:16])[CH2:11][CH2:12][CH3:13]

Participants

4

Reactant 2

HCID 33855-FluorouracilHCID 8110Butyl isocyanate

Product 1

HCID 1165421(2H)-Pyrimidinecarboxamide, N-butyl-5-fluoro-3,4-dihydro-2,4-dioxo-Yield 72.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

13.0g (0.10 mole) of 5-fluorouracil was dissolved in 70 ml of dimethyl formamide, then 11.9g (0.12 mole) of n-butyl isocyanate was added thereto at room temperature and stirred at the same temperature for 24 hours. The reaction mixture was concentrated to 40ml by removing dimethyl formamide and excess n-butyl isocyanate under reduced pressure. The residue was poured into 300ml of water and resultant precipitate was filtered off. The precipitate was washed and dried and 16.6g (72.3% yield) of 1-(n-butylcarbamoyl)-5-fluorouracil was obtained

Workup

  1. concentrationThe reaction mixture was concentrated to 40ml
  2. customby removing dimethyl formamide and excess n-butyl isocyanate under reduced pressure
  3. additionThe residue was poured into 300ml of water and resultant precipitate
  4. filtrationwas filtered off
  5. washThe precipitate was washed
  6. customdried

Sources & evidence

ORD record
ord-d9b1029cb8e94d3ca81e29df96f4a0d7
Source dataset
uspto-grants-1978_01
Patent number
US04071519

Reaction notes

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