Nitrogen → HCID 86697417, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of (3-bromo-pyrazolo[1,5-a]pyrimidin-5-yl)-butyl-amine (350.3 mg, 1.3 mmol), 4-aminomethylphenylboronic acid, hydrochloride [75705-21-4] (337.1 mg, 1.8 mmol), potassium phosphate tribasic monohydrate [27176-10-9] (601.6 mg, 2.6 mmol), and [1,1′-bis(diphenylphosphino) ferrocene]dichloropalladium(II), complex with dichloromethane [95464-05-4] (117.2 mg, 0.1 mmol) contained in a 50 mL round bottomed flask was added a solution of 30% (v/v) water in 1,2-dimethoxyethane (25 mL) and a magnetic stir bar. The reaction pot was fitted to a reflux condenser, lowered into an ambient temperature oil bath, and the system taken through 10 evacuation/N2 blanket cycles while being rapidly stirred. The rapidly stirred, N2 blanketed, reaction was heated to an oil bath temperature of 85° C. for 17 h then cooled and partitioned between brine and ethyl acetate. The phase separated extract was dried (MgSO4) and evaporated to afford a brown oil which was purified by preparative RP-HPLC to yield 71.9 mg of [3-(4-Aminomethyl-phenyl)-pyrazolo[1,5-a]pyrimidin-5-yl]-butyl-amine monoacetate salt as a white solid, mp. 171-172° C. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.97 (t, J=7.39 Hz, 3 H) 1.43 (sxt, J=7.36 Hz, 2 H) 1.64 (quin, J=7.17 Hz, 2 H) 3.43 (q, J=6.47 Hz, 2 H) 3.71-3.84 (m, 2 H) 6.29 (d, J=7.50 Hz, 1 H) 7.34 (m, J=8.16 Hz, 2 H) 7.62-7.71 (m, 1 H) 8.05 (m, J=7.94 Hz, 2 H) 8.32 (s, 1 H) 8.46 (d, J=7.50 Hz, 1 H).

Provenance & Evidence