N,N-Dimethylaniline → 7-Chloro-5-(furan-2-yl)-2-phenylpyrazolo[1,5-a]pyrimidine

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-(furan-2-yl)-2-phenylpyrazolo[1,5-a]pyrimidin-7(4H)-one (0.277 g, 1.0 mmol, 1.0 eq), POCl3 (0.613 g, 4.0 mmol, 4.0 eq), N-benzyl-N,N,N-triethylethanaminium chloride (0.456 g, 2.0 mmol, 2.0 eq) and N,N-dimethylaniline (0.121 g, 1.0 mmol, 1.0 eq) in acetonitrile (5.0 mL) was heated at 80° C. for 4 hr. The completed reaction was diluted with CHCl3 (20 mL), washed with H2O (10 mL), and the separated organic layers were dried (MgSO4) and concentrated. The residue was purified by chromatography (Biotage25 g, EtOAc/Hexane) to afford 7-chloro-5-(furan-2-yl)-2-phenylpyrazolo[1,5-a]pyrimidine (0.247 g, 84%) as a yellow solid. 1H-NMR (400 MHz, CDCl3) δ 7.97-7.94 (m, 2H), 7.56 (m, 1H), 7.43-7.39 (m, 2H), 7.36-7.34 (m, 1H), 7.19 (s, 1H), 7.17 (dd, J=3.5, 0.5 Hz, 1H), 6.97 (s, 1H), 6.54 (dd, J=3.5, 1.7 Hz, 1H).

Provenance & Evidence