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

Participants

Reaction Steps

To a solution of 4-(2-amino-pyrimidin-5-yl)-N1-tert-butyl-benzene-1,2-diamine (100 mg, 0.39 mmol) in DMF (3 mL) is added 2-(5-methyl-1,3,4-thiadiazol-2-yl)-benzaldehyde (100 mg, 0.49 mmol) at room temperature. Oxone (240 mg, 0.39 mmol) in H2O (1 mL) is added and the solution is stirred at the same temperature for 3 hours. The reaction is poured into water (75 mL) and sodium thiosulfate (sat., 15 mL). The product is extracted into EtOAc (3×) and the combined organics are then dried (MgSO4), filtered, and concentrated. Purification via flash chromatography (12 g silica gel, 0-10% MeOH/CH2Cl2) gives impure product which is re-purified via preparative TLC (0.5 mm silica gel, 5% MeOH/CH2Cl2). The product band is isolated to give the title compound (23 mg, 13%). LCMS (ESMS): m/z 442.20 (M++1)

Provenance & Evidence