5-Fluorouracil → 5-Fluoro-3-methylpyrimidine-2,4(1H,3H)-dione

HRID 2165109Notes

Reaction equation

HRID 2165109 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]=1

Participants

5

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

  1. customThe reaction solution obtained
  2. filtrationwas filtered
  3. customto remove potassium carbonate
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. 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

Loading…