Hydrochloric Acid → HCID 178483078, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of cis-4-(4-dimethylamino-quinazolin-2-ylamino)-cyclohexanecarboxylic acid amide (18.78 g, 60 mmol) in THF (200 mL) was added a solution of 1 M BH3 in THF (300 mL, 300 mmol). The mixture was stirred at reflux for 2 hr. After cooling the reaction mixture to 0° C., 4 M HCl in EtOAc (100 mL) and MeOH (200 mL) were added. The mixture was concentrated. The mixture was treated with 1 M aqueous sodium hydroxide and the aqueous layer was extracted with CH2Cl2. The organic layer was dried over sodium sulfate, concentrated, and purified by column chromatography (silica gel, 10% 2 M NH3/MeOH in CH2Cl2) to give cis-N2-(4-aminomethyl-cyclohexyl)-N4,N4-dimethyl-quinazoline-2,4-diamine as a white solid (10.6 g, 59%).

Provenance & Evidence