Ethyl Acetoacetate → HCID 178429161, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of 3-(3-chlorophenyl)-1H-pyrazol-5-amine (10 g, 51.6 mmol) and ethyl 3-oxobutanoate (26.3 ml, 207 mmol) in o-xylene (200 mL) was heated at reflux (oil bath temp: 155-160° C.) for 20 h. Note: The reaction turned clear solution between 60-70° C. and solids started crashing out at 130° C. Then, cooled, diluted with hexanes (100 mL), filtered, washed with hexanes (100 mL) and dried to afford 2-(3-chlorophenyl)-5-methylpyrazolo[1,5-a]pyrimidin-7-ol (11.8 g, 45.4 mmol, 88% yield) as off-white solid. 1H NMR (400 MHz, DMSO-d6) δ: 12.46 (s, 1H), 8.05 (s, 1H), 8.00-7.95 (m, 1H), 7.56-7.45 (m, 2H), 6.70 (s, 1H), 5.64 (s, 1H), 2.33 (s, 3H). LCMS (M+H) calcd for C13H11ClN6O: 260.06. found: 260.1.

Provenance & Evidence