5-Fluorouracil → 5-Fluoro-3-methylpyrimidine-2,4(1H,3H)-dione
Reaction equation
[F:1][C:2]1[C:3](=[O:9])[NH:4][C:5](=[O:8])[NH:6][CH:7]=1.CI.[C:12](=O)([O-])[O-].[K+].[K+]>CC(C)=O>[F:1][C:2]1[C:3](=[O:9])[N:4]([CH3:12])[C:5](=[O:8])[NH:6][CH:7]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
5-Fluorouracil, namely Compound (5) (1.30 g; 10 mmol), methyl iodide (CH3I) (2.13 g; 15 mmol) and potassium carbonate (0.69 g; 5 mmol) were added to acetone (20 ml), and the resulting mixture was stirred at 60°-70° C. for 24 hours. The reaction solution obtained was filtered to remove potassium carbonate, and the filtrate was concentrated under reduced pressure. To the resulting residue was added a small volume of chloroform, and then the residue was fractionated by column chromatography on silica gel (eluent: chloroform) to isolate 5-fluoro-3-methyluracil, namely Compound (6) shown above (355 mg) as white needle-like crystals.
Workup
- customThe reaction solution obtained
- filtrationwas filtered
- customto remove potassium carbonate
- concentrationthe filtrate was concentrated under reduced pressure
- additionTo the resulting residue was added a small volume of chloroform
Sources & evidence
- ORD record
- ord-1f6de000aa7344ecb77eec94ea2b3e54
- Source dataset
- uspto-grants-1990_07
- Patent number
- US04939156
Reaction notes
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