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

HRID 22253Notes

Reaction equation

HRID 22253 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-9d2f75daf53a415781fd49767dae3cc6
Source dataset
uspto-grants-1995_06
Patent number
US05428037

Reaction notes

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