Phosphorus oxychloride → 6-Butyl-4-chloro-2-methyl-5-[(4-iodophenyl)methyl]pyrimidine
Reaction equation
[CH2:1]([C:5]1[N:10]=[C:9]([CH3:11])[NH:8][C:7](=O)[C:6]=1[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([I:20])=[CH:16][CH:15]=1)[CH2:2][CH2:3][CH3:4].O=P(Cl)(Cl)[Cl:23]>>[CH2:1]([C:5]1[N:10]=[C:9]([CH3:11])[N:8]=[C:7]([Cl:23])[C:6]=1[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([I:20])=[CH:16][CH:15]=1)[CH2:2][CH2:3][CH3:4]Participants
3
Procedure
A solution of 485 mg (1.27 mmol) 6-butyl-2-methyl-5-[(4-iodophenyl)methyl]pyrimidine-4(3H)-one in 7 mL POCl3 was refluxed for 60 minutes. After cooling to room temperature, excess POCl3 was stripped off in vacuo. The crude product was partitioned between CH2Cl2 and a mixture of brine and NaHCO3. The organic layer was removed and the aqueous layer was extracted three more times with CH2Cl2. The combined organic material was dried over MgSO4, stripped of solvent in vacuo, then was medium pressure chromatographed on silica gel using 10% EtOAc/hexane to give 380 mg of 6-butyl-4-chloro-2-methyl-5-[(4-iodophenyl)methyl]pyrimidine, 75% yield.