Sodium Thiosulfate → 5-[2-(2-bromo-phenyl)-1-tert-butyl-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 (1 g, 3.89 mmol) in DMF (30 mL) is added 2-bromobenzaldehyde (0.7 mL, 5.83 mmol) at room temperature. Oxone (2.4 g, 3.89 mmol) in H2O (5 mL) is added and the solution is stirred for 1 hour. Saturated sodium thiosulfate solution (10 mL) is added and the mixture is extracted with EtOAc (3×15 mL) and H2O (20 mL). The combined organic layer is dried (MgSO4), filtered and concentrated. The residue is purified by silica gel flash column chromatography eluting with 10% MeOH in CH2Cl2 to afford 5-[2-(2-bromo-phenyl)-1-tert-butyl-1H-benzimidazol-5-yl]-pyrimidin-2-ylamine (800 mg, 48%) as a white solid.

Provenance & Evidence