Water → 5-Fluoro-4-hydroxy-2-oxo-N-(propan-2-yl)pyrimidine-1(2H)-carboximidic acid

HRID 1834765Notes

Reaction equation

HRID 1834765 reaction equation
[F:1][C:2]1[C:3](=[O:9])[NH:4][C:5](=[O:8])[NH:6][CH:7]=1.[CH:10]([N:13]=[C:14]=[O:15])([CH3:12])[CH3:11].O>CS(C)=O>[F:1][C:2]1[C:3](=[O:9])[NH:4][C:5](=[O:8])[N:6]([C:14](=[O:15])[NH:13][CH:10]([CH3:12])[CH3:11])[CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 33855-FluorouracilHCID 61277Isopropyl isocyanate

Product 1

HCID 1515285-Fluoro-4-hydroxy-2-oxo-N-(propan-2-yl)pyrimidine-1(2H)-carboximidic acidYield 68.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

13.0g (0.1 mole) of 5-fluorouracil was dissolved in 100ml of dimethyl sulfoxide, then 9.4g (0.11mole) of isopropyl isocyanate was added thereto at room temperature and stirred at the same temperature for 15 hours. The reaction mixture was poured into 800ml of water. The resultant precipitate was filtered off, washed with water and dried to give 14.7g (68.5% yield) of 5-fluoro-1-(iso-propylcarbamoyl)-uracil melting at 275°-285° C (decomposition).

Workup

  1. filtrationThe resultant precipitate was filtered off
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-b42e7e17a7614223987f4a7a6da207d7
Source dataset
uspto-grants-1978_01
Patent number
US04071519

Reaction notes

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