Sodium Bicarbonate → 5-{1-tert-Butyl-2-[2-(4-chloro-pyrazol-1-yl)-5-methoxy-phenyl]-1H-benzimidazol-5-yl}-pyrimidin-2-ylamine

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Reaction Steps

A solution of 4-(2-amino-pyrimidin-5-yl)-N1-tert-butyl-benzene-1,2-diamine (180 mg, 0.70 mmol) and 2-(4-chloro-pyrazol-1-yl)-5-methoxy-benzaldehyde (270 mg, 1.14 mmol) in acetic acid (5 mL) is warmed to 100° C. for 16 hours, then cooled to room temperature and neutralized with NaHCO3 (sat.). The product is extracted into EtOAc (3×) and the combined organics are dried (MgSO4), filtered and concentrated. Purification via flash chromatography (12 g silica gel, 0-5% MeOH/CH2Cl2) follows by reverse phase HPLC (20-100% CH3CN/H2O, each solvent containing 0.1% TFA) affords the title compound (90 mg, 27%). LCMS (ESMS): m/z 474.20 (M++1)

Provenance & Evidence