2-Methylpyrrolidine → 4-(2-hydroxypropan-2-yl)-N-(7-(2-methylpyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide

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A solution of N-(7-chloropyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide (2D, 50 mg, 151 mmol) and 2-methylpyrrolidine (26 mg, 0.302 mmol) in NMP (0.950 mL) was stirred at 85° C. overnight. After cooling to room temperature, the mixture was diluted with a few drops of DMSO and methanol, and was then purified by preparatory HPLC, 25-50% (MeCN/H2O gradient+0.01% TFA). Lyophilization of the combined fractions gave the titled compound as a orange solid (34 mg, 59%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.26 (d, J=6.06 Hz, 3H) 1.45 (s, 6H) 1.71-1.81 (m, 1H) 1.90-2.01 (m, 1H) 2.03-2.26 (m, 2H) 3.75-3.91 (m, 1H) 3.96-4.12 (m, 1H) 4.96 (br. s., 1H) 6.27 (d, J=2.27 Hz, 1H) 6.98 (s, 1H) 7.61 (d, J=8.34 Hz, 2H) 7.91-8.09 (m, 3H) 10.81 (s, 1H). ESI-MS: m/z 380.3 (M+H)+.

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