Phosphorus oxychloride → 4-Chloro-6-phenylfuro[2,3-d]pyrimidine
Reaction equation
[C:1]1([C:7]2[O:16][C:10]3[N:11]=[CH:12][NH:13][C:14](=O)[C:9]=3[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O=P(Cl)(Cl)[Cl:19]>>[Cl:19][C:14]1[C:9]2[CH:8]=[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[O:16][C:10]=2[N:11]=[CH:12][N:13]=1Participants
3
Conditions
- Temperature
- 60 °C
Procedure
A mixture of 6-phenylfuro[2,3-d]pyrimidin-4(3H)-one (1.0 g) and POCl3 (10 mL) was stirred at 55-65° C. for 3 h. The reaction mixture was poured into ice cold water and stirred for 10 min. The solution was extracted with chloroform (3×100 mL) and the combined chloroform layer was washed with aq. NaHCO3 solution, water, brine and dried over sodium sulfate. The residue was chromatographed over silica gel column using hexane-EtOAc (95:5) as eluents to give the product as a white color solid (800 mg, 74%), mp 136-138° C. 1H NMR (400 MHz, CDCl3): δ 8.74 (1H, s), 7.90-7.93 (2H, m), 7.45-7.54 (3H, m), 7.08 (1H, s).