Sodium Carbonate → 3-(4-(4-aminopyrimidin-5-yl)-1H-pyrazolo[3,4-b]pyridin-1-yl)benzenesulfonamide

Participants

Reaction Conditions

Reaction Steps

Example 4 was prepared according to the general procedure of Example 1, except heating at 105° C. for 18 h and using the following materials: Intermediate 1B (32 mg, 0.101 mmol), 4-amino-5-bromopyrimidine (38.6 mg, 0.222 mmol), sodium carbonate (41.8 mg, 0.394 mmol), EtOH:DME:H2O (1.2:2.5:1.0 ratio) (1.0 mL) and tetrakis(triphenylphosphine) palladium(0) (18.6 mg, 0.016 mmol). The title compound was isolated as a white solid (4.3 mg, 11.6%). Purification was done by preparative HPLC (Condition A) using a Phenomenex Luna Axia 30×100 mm S10 column from 5% Solvent B to 100% Solvent B over 12 min, ret. T=4.7 min. 1H NMR (500 MHz, DMSO-d6) δ ppm 8.75-8.87 (2 H, m), 8.62-8.71 (1 H, m), 8.52 (1 H, s), 8.42 (1 H, s), 8.28 (1 H, s), 7.79-7.84 (2 H, m), 7.57 (2 H, s), 7.47 (1 H, d, J=4.88 Hz), 6.97 (2 H, br. s.) LC/MS (Condition B): ret. T=1.6 min, (M+H)+ 367.97. Analytical HPLC: (Condition A): >99%, ret. T=11.81 min, (Condition B): >99%, ret. T=13.74 min, (Condition C): >99%, ret. T=3.87 min, (Condition D): >99%, ret. T=4.18 min.

Provenance & Evidence