6-Methyluracil → 5-Fluoro-6-methylpyrimidine-2,4-diol

HRID 1075784Notes

Reaction equation

HRID 1075784 reaction equation
[CH3:1][C:2]1[NH:7][C:6](=[O:8])[NH:5][C:4](=[O:9])[CH:3]=1.[F:10]F>O>[F:10][C:3]1[C:4](=[O:9])[NH:5][C:6](=[O:8])[NH:7][C:2]=1[CH3:1]

Participants

4

Reactant 2

HCID 122836-MethyluracilHCID 24524Fluorine2×

Product 1

HCID 2338935-Fluoro-6-methylpyrimidine-2,4-diol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The preceding example was substantially repeated but at a lower reaction temperature. A suspension of 6-methyl uracil (4.00g) in water (30 ml) was maintained at 0°-10°C and fluorinated with a stream of fluorine and nitrogen, present in equal volumes, until fluorine was detected at the reactor outlet. The reaction mixture was allowed to stand for two days at room temperature and 1.05g of crystals were collected and found to have a different IR spectrum than the starting material. A DSC analysis showed 2 transitions at 313°C and 318°C followed by apparent decomposition. The structure of the product was identified as 5-fluoro-6-methyl uracil by NMR analysis.

Workup

  1. temperaturewas maintained at 0°-10°C
  2. custom1.05g of crystals were collected
  3. customat 313°C
  4. custom318°C

Sources & evidence

ORD record
ord-e0e30c37034847b09d50279a7227833d
Source dataset
uspto-grants-1976_05
Patent number
US03954758

Reaction notes

Loading…