Bromine → 5-Bromo-3-methyl-6-phenyl-4-pyrimidinone

HRID 1981587Notes

Reaction equation

HRID 1981587 reaction equation
N[C:2]1[N:7]([CH3:8])[C:6](=[O:9])[CH:5]=[C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:3]=1.[Br:16]Br>CC(O)=O>[Br:16][C:5]1[C:6](=[O:9])[N:7]([CH3:8])[CH:2]=[N:3][C:4]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 133205052-Amino-3-methyl-6-phenyl-4-pyrimidinone

Product 1

HCID 233196395-Bromo-3-methyl-6-phenyl-4-pyrimidinoneYield 42.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To 1.8 g (8.95 mM) of 2-amino-3-N-methyl-6-phenyl-4-pyrimidinone was added 40 ml CH3COOH and 0.535 ml Br2 (1.64 g≈10.3 mM). The reaction mixture was allowed to stir at ambient temperature for 18 hours. The solution was evaporated to dryness and the residual solid azeotroped from EtOH (2X). The solids were heated to reflux with 100 ml of H2O, cooled to 5° and filtered. This procedure was repeated, filtered hot, and allowed to crystallize at room temperature for 18 hours. The crystals were filtered and washed well with H2O to yield 1.0 g (40%) of title compound. Cooling of mother liquors gave an additional 0.6 g (24%) of title compound.

Workup

  1. customThe solution was evaporated to dryness
  2. customthe residual solid azeotroped from EtOH (2X)
  3. temperatureThe solids were heated
  4. temperatureto reflux with 100 ml of H2O
  5. temperaturecooled to 5°
  6. filtrationfiltered
  7. filtrationfiltered hot
  8. customto crystallize at room temperature for 18 hours
  9. filtrationThe crystals were filtered
  10. washwashed well with H2O

Sources & evidence

ORD record
ord-30bd46901dff47dd969fadecbb88551e
Source dataset
uspto-grants-1986_06
Patent number
US04593096

Reaction notes

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