Cesium carbonate → 4-amino-6-[[(1S)-1-[6-fluoro-7-(1H-indazol-4-yl)-1-methyl-benzimidazol-2-yl]ethyl]amino]pyrimidine-5-carbonitrile

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A mixture of 4-amino-6-[(S)-1-(7-bromo-6-fluoro-1-methyl-1H-benzoimidazol-2-yl)ethylamino]pyrimidine-5-carbonitrile, (0.10 g, 0.26 mmol), 1H-indazole-4-boronic acid (0.054 g, 0.33 mmol), tetrakis(triphenylphosphine)palladium(0) (0.015 g, 0.013 mmol) and caesium carbonate (0.17 g, 0.51 mmol) in dioxane (3 mL) and water (1.5 mL) was placed in a sealed tube and degassed with nitrogen for 5 minutes, then heated for 30 min at 140° C. by microwave irradiation. 1H-indazole-4-boronic acid (0.054 g, 0.33 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.015 g, 0.01 mmol) were added and the resultant mixture heated for 30 min at 140° C. by microwave irradiation. The resulting mixture was loaded onto an Isolute® SCX-2 cartridge then washed with MeOH and the product eluted with 2M NH3/MeOH and concentrated in vacuo. The residue was purified by preparative HPLC (Phenomenex Gemini 5 μm C18 on a 78 min gradient 20-98% 0.1% HCO2H in acetonitrile/water) to give 426 as a white solid (0.044 g, 40%). LCMS (Method K): RT 2.82, 2.99 min [M+H]+ 428.1. 1H NMR (DMSO-d6, 400 MHz): δ 13.30 (1H, s), 8.23-7.98 (1H, m), 7.77-7.60 (4H, m), 7.51-7.48 (1H, m), 7.36-7.24 (2H, m), 7.23-7.08 (2H, m), 5.59-5.54 (1H, m), 3.00 (3H, d, J=8.05 Hz), 1.57 (3H, dd, J=6.69, 1.65 Hz). Signals split due to presence of rotamers/tautomers

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