Sodium Thiosulfate → 5-[1-tert-butyl-2-(2-iodo-phenyl)-1H-benzimidazol-5-yl]-pyrimidin-2-ylamine

Participants

Reaction Steps

To a round bottom flask are added 4-(2-amino-pyrimidin-5-yl)-N1-tert-butyl-benzene-1,2-diamine (430 mg, 1.67 mmol) in DMF (10 mL) and water (3 mL), followed by the addition of 2-iodobenzaldehyde (445 mg, 1.92 mmol) and oxone (1180 mg, 1.92 mmol). The reaction mixture is stirred at room temperature for 1 hour. Saturated sodium thiosulfate (10 mL) is added. The reaction mixture is diluted with EtOAc (50 mL). The organic layer is washed with water, brine, dried under anhydrous Na2SO4, filtered and concentrated. The residue is purified by silica gel flash column chromatography with 0-5% MeOH/CH2Cl2 as the eluent. The product fractions are collected and concentrated to afford 5-[1-tert-butyl-2-(2-iodo-phenyl)-1H-benzimidazol-5-yl]-pyrimidin-2-ylamine (270 mg, 34%) as a light brown solid. LCMS (ESMS): m/z 470.58 (M++1)

Provenance & Evidence