Phosphorus oxychloride → 4,5-Dimethyl-6-chloro-2-(4-methylphenyl)pyrimidine

HRID 1077835Notes

Reaction equation

HRID 1077835 reaction equation
[CH3:1][C:2]1[C:3](=O)[NH:4][C:5]([C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)=[N:6][C:7]=1[CH3:8].P(Cl)(Cl)([Cl:19])=O>>[CH3:8][C:7]1[C:2]([CH3:1])=[C:3]([Cl:19])[N:4]=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)[N:6]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 1357047395,6-dimethyl-2-(4-methylphenyl)-3H-pyrimidin-4-one

Product 1

HCID 194302834,5-Dimethyl-6-chloro-2-(4-methylphenyl)pyrimidine

Procedure

A mixture of 5,6-dimethyl-2-(4-methylphenyl)-3H-pyrimidin-4-one (6 g) and phosphorus oxychloride (40 ml) was refluxed for 2 hours. Excess phosphorus oxychloride was removed under reduced pressure, ice added to the residue, and the mixture extracted with methylene chloride, the organic layer washed with brine, dried over sodium sulfate, the solvent evaporated under reduced pressure, to yield 6.2 g of 4,5-dimethyl-6-chloro-2-(4-methylphenyl)pyrimidine, m.p. 165° C.

Workup

  1. temperaturewas refluxed for 2 hours
  2. customExcess phosphorus oxychloride was removed under reduced pressure, ice
  3. additionadded to the residue
  4. extractionthe mixture extracted with methylene chloride
  5. washthe organic layer washed with brine
  6. dry with materialdried over sodium sulfate
  7. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-889be9c1327f49c98791498eed318eb0
Source dataset
uspto-grants-1996_08
Patent number
US05545645

Reaction notes

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