N,N-Dimethylaniline → HCID 86667838, compound

Participants

Reaction Steps

4-(7-Hydroxy-pyrazolo[1,5-a]pyrimidin-5-yl)-cyclohexanecarboxylic acid t-butyl ester (Int-7b, 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 was reduced in vacuo and cooled to 0° C. in ice bath. The reaction was then quenched with sat. NaHCO3(aq) and extracted with DCM (100 mL×3). The combined organics were dried with Na2SO4 and the solvent was removed in vacuo. The resulting oil was purified via silica gel column on 20% to 100% ethyl acetate in hexanes gradient to yield the title compound (2.5 g, 32% over three steps). LC-MS: 336 [M+H].

Provenance & Evidence