N,N-Dimethylaniline → HCID 86664779, compound

Participants

Reaction Steps

4-(7-Hydroxy-pyrazolo[1,5-a]pyrimidin-5-yl)-cyclohexanecarboxylic acid methyl ester (10.6 g), N,N-dimethylaniline (15.0 ml) and POCl3 (120 mL) were mixed and stirred at room temperature for 18 hours. The solution is reduced in vacuo and cooled to 0° C. in ice bath. The reaction is then quenched with sat. NaHCO3(aq) and extracted with DCM (100 mL×3). The combined organics are dried with Na2SO4 and the solvent removed in vacuo. The resulting oil was purified via silica gel column on 20% to 100% ethyl acetate in hexanes gradient to yield the titled compound (2.5 g, 32% over three steps). LC-MS: 294 [M+H].

Provenance & Evidence