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

HRID 1763947Notes

Reaction equation

HRID 1763947 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 (4.00 g) 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 1.05 g 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. custom1.05 g of crystals were collected
  3. customat 313° C.
  4. custom318° C.

Sources & evidence

ORD record
ord-b41060b5f54b4cd594ddfc40259e85e8
Source dataset
uspto-grants-1978_09
Patent number
US04113949

Reaction notes

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