N,N-Dimethylaniline → 7-Chloro-5-(1,4-dioxaspiro[4.5]decan-8-yl)pyrazolo[1,5-a]pyrimidine

Participants

Reaction Steps

5-(1,4-dioxaspiro[4.5]decan-8-yl)pyrazolo[1,5-a]pyrimidin-7-ol (Int-5e, 11.7 mmol) was charged to 250 mL round-bottom flask. To this flask was added 4 mL N, N-dimethylaniline, followed by 40 mL POCl3. This suspension was sonicated to break up the starting material and stirred at room temperature for 18 hours. After 18 hours, all starting material had dissolved. The solution was reduced in vacuo and cooled to 0° C. in an ice bath. The reaction was then quenched with sat. NaHCO3(aq) and extracted with DCM (x3). The combined organics were dried over Na2SO4 and the solvent was removed in vacuo. The resulting oil was purified via silica gel column with a 20% to 100% ethyl acetate in hexanes gradient to yield 7-chloro-5-(1,4-dioxaspiro[4.5]decan-8-yl)pyrazolo[1,5-a]pyrimidine (Int-5f) (2.65 grams, 77% across 2 steps) as a white solid.

Provenance & Evidence