Acetic Acid → HCID 178483062, compound

Participants

Reaction Steps

To a solution of trans-N2-(4-aminomethyl-cyclohexylmethyl)-N4,N4-dimethyl-quinazoline-2,4-diamine (500 mg, 1.59 mmol) in CH2Cl2 (5 mL) were added 4-bromo-2-trifluoromethoxy-benzaldehyde obtained in step A of example 13 (428 mg, 1.59 mmol), acetic acid (95 mg, 1.59 mmol), and NaBH(OAc)3 (505 mg, 2.38 mmol). The reaction mixture was stirred at ambient temperature for 4 hr. The reaction was quenched with saturated aqueous NaHCO3. The aqueous layer was extracted with CHCl3 (three times). The combined organic layer was dried over MgSO4, filtered, concentrated, and purified by flash chromatography (NH-silica gel, 50% EtOAc in hexane) to give trans-N2-{4-[(4-bromo-2-trifluoromethoxy-benzylamino)-methyl]-cyclohexylmethyl}-N4,N4-dimethyl-quinazoline-2,4-diamine (783 mg, 89%) as a pale yellow solid.

Provenance & Evidence