Phosphorus oxychloride → 4-Chloro-2-methyl-6-phenylpyrimidine

HRID 2063599Notes

Reaction equation

HRID 2063599 reaction equation
[CH3:1][C:2]1[NH:7][C:6](=O)[CH:5]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:3]=1.O=P(Cl)(Cl)[Cl:17]>>[Cl:17][C:6]1[CH:5]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:3]=[C:2]([CH3:1])[N:7]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 1354430772-Methyl-6-phenyl-4-pyrimidinol

Product 1

HCID 7961284-Chloro-2-methyl-6-phenylpyrimidine

Procedure

A mixture of 2-methyl-6-phenylpyrimidin-4(3H)-one (15 g) and POCl3 (150 ml) was refluxed under nitrogen for 20 h. The excess POCl3 was distilled off and the residue was diluted with ethyl acetate (500 ml) and washed with 10% solution of sodium bicarbonate (100 ml), water, brine and dried. The solvent was removed under reduced pressure and the residue was purified by chromatography (silica, 60-120 mesh) eluting with pet ether/ethyl acetate (9/1) to afford 11 g (67%) of the titled as a pale yellow solid.

Workup

  1. temperaturewas refluxed under nitrogen for 20 h
  2. distillationThe excess POCl3 was distilled off
  3. additionthe residue was diluted with ethyl acetate (500 ml)
  4. washwashed with 10% solution of sodium bicarbonate (100 ml), water, brine
  5. customdried
  6. customThe solvent was removed under reduced pressure
  7. customthe residue was purified by chromatography (silica, 60-120 mesh)
  8. washeluting with pet ether/ethyl acetate (9/1)
  9. customto afford 11 g (67%) of the

Sources & evidence

ORD record
ord-3eb7dbdd86134f718aec396d3c97aa72
Source dataset
uspto-grants-2012_10
Patent number
US08288398B2

Reaction notes

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