Phosphorus oxychloride → 4-Chloro-2-methyl-6-phenylpyrimidine
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]=1Participants
3
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
- temperaturewas refluxed under nitrogen for 20 h
- distillationThe excess POCl3 was distilled off
- additionthe residue was diluted with ethyl acetate (500 ml)