4-Phenyl-1H-pyrazol-5-amine → Methyl2-(7-hydroxy-5-methyl-3-phenyl-4,7-dihydropyrazolo[1,5-a]pyrimidin-6-yl)acetate

Participants

Reaction Steps

To a solution of 4-phenyl-1H-pyrazol-5-amine (0.5 g, 3.14 mmol) and dimethyl 2-acetylsuccinate (1.77 g, 9.4 mmol) in xylene (100 mL) was added p-toluenesulfonic acid monohydrate (5 mg, 0.263 mmol). The reaction mixture was heated at reflux under a Dean-Stark trap for 20 hrs. The solid was filtered and washed by hexanes to afford (0.75 g, 80%) of the title compound. 1H-NMR (500 MHz, DMSO-d6) δ ppm 2.38 (3H, s), 3.39 (2H, s), 3.59 (3H, s), 7.33 (1H, S), 7.47 (2H, m), 7.57 (2H, m) 8.13 (1H, S), 11.87 (1H, s).

Provenance & Evidence