Water → 5-{1-tert-Butyl-2-[5-methoxy-2-(3-methyl-1,2,4-thiadiazol-5-yl)-phenyl]-1H-benzimidazol-5-yl}-pyrimidin-2-ylamine

Participants

Reaction Steps

A solution of 4-(2-amino-pyrimidin-5-yl)-N1-tert-butyl-benzene-1,2-diamine (110 mg, 0.43 mmol) and 5-methoxy-2-(3-methyl-1,2,4-thiadiazol-5-yl)-benzaldehyde (100 mg, 0.43 mmol) in acetic acid (5 mL) is warmed to 50° C. for 12 hours then at 80° C. for 60 hours. The reaction mixture is cooled to room temperature and poured into water and 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) affords the title compound (40 mg, 20%). LCMS (ESMS): m/z 472.20 (M++1)

Provenance & Evidence