NaH (60% in mineral oil, 13 mg, 0.314 mmol) was added in one portion to a mixture of 1H-pyrazolo[3,4-d]pyrimidin-4-ylamine (42 mg, 0.314 mmol) in DMF (5 mL) at RT. After 5 min stirring a solution of methanesulfonic acid 3-phenylbenzo[b]thiophen-2-ylmethyl ester from Example 26 (100 mg, 0.314 mmol) in DMF (1 mL) was added dropwise and stirring at RT was continued for 30 min. The reaction mixture was then quenched by addition of water and diluted with EtOAc. The aqueous phase was further extracted with EtOAc (2×100 mL) and the combined organic layers were washed with brine, then dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-10% MeOH in EtOAc) and triturated from MeOH with water affording 164 as an off-white solid (17 mg, 15%). LCMS: RT 4.13 min [M+H]+ 358.1. 1H NMR (DMSO, 400 MHz): δ 8.23 (1H, s), 8.16 (1H, s), 7.95-7.90 (1H, m), 7.70-7.59 (4H, m), 7.56-7.49 (2H, m), 7.42-7.35 (2H, m), 5.72 (2H, s)
