Butylamine → HCID 86697416, compound

Participants

Reaction Steps

A solution of 5-chloro-pyrazolo[1,5-a]pyrimidine [29274-24-] (955.4 mg, 6.2 mmol) in butylamine [109-73-9] (6.2 mL, 62.7 mmol), under N2 blanket, was magnetically stirred at 65° C. for 17 h then partitioned between brine (pH adjusted to 10 with saturated aqueous sodium bicarbonate) and ethyl acetate. The phase separated extract was dried (MgSO4) and diluted with heptane to precipitate butyl-pyrazolo[1,5-a]pyrimidin-5-yl-amine as 1.2 g of yellow powder, mp. 75-76° C. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.91 (t, J=7.33 Hz, 3 H) 1.37 (dq, J=15.00, 7.29 Hz, 2 H) 1.47-1.59 (m, 2 H) 3.24-3.34 (m, 2 H) 5.94 (d, J=1.52 Hz, 1 H) 6.22 (d, J=7.58 Hz, 1 H) 7.35 (br. s., 1 H) 7.74 (d, J=2.27 Hz, 1 H) 8.40 (d, J=7.58 Hz, 1 H). 13C NMR (100 MHz, DMSO-d6) δ ppm 13.69, 19.71, 30.65, 91.00, 99.95, 134.70, 143.45, 148.37, 155.43. LRMS (ESI) m/z 191.1 [(M+H)]+, calc'd for C10H14N4: 190.25

Provenance & Evidence