40 mg (0.11 mmol) of 2-amino-5-[3-(2-methoxy-phenyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-benzoic acid and 63 mg (0.16 mmol) of O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyl-uronium hexafluorophosphate were dissolved in 2 mL of DMF. 40 μL (30 mg, 0.23 mmol) of di-iso-propyl ethyl amine and 100 μL (70 mg, 0.96 mmol) of diethylamine were added and the resulting mixture irradiated in a Personal Chemistry® Optimizer to 130° C. for 30 min. The resulting mixture was distributed between a saturated aqueous solution of sodium bicarbonate and dichloromethane and the organic phase was dried over sodium sulfate and evaporated. The resulting crude was purified by mass-triggered reverse-phase HPLC to afford 3.2 mg (7.7 μmol, 7%) of 2-amino-N,N-diethyl-5-[3-(2-methoxy-phenyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-benzamide as an off-white solid. 1H NMR (500 MHz, DMSO-d6) δ 13.72 (s, br., 1H), 8.75 (d, 1H), 8.17 (d, 1H), 7.64 (dd, 1H), 7.49 (dd, 1H), 7.46 (ddd, 1H), 7.32 (d, 1H), 7.21 (d(d), 1H), 7.09 (ddd, 1H), 6.85 (d, 1H), 3.84 (s, 3H), 3.4-3.3 (m, 4H), 1.15-1.05 (m, br., 6H), MS: m/z 416.1 (M+H+).
