Hydrochloric Acid → HCID 22249265, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 2-methylthio-4-[benzylamino]-pyrimidine-5-carboxylate (0.1 g, 0.3 mmol, Step A) in EtOH (3 mL) was added 1 mL of aq. 1N NaOH solution. The resulting mixture was stirred at 45° C. for 2 h. The resulting mixture was neutralized with aq. 1N HCl and concentrated. To the residue in 3 mL of CH2Cl2 was added 4-isopropylaniline (90 mg, 0.66 mmol), HATU (0.18 g, 0.45 mmol), and 0.5 mL of TEA (0.36 g, 3.5 mmol). The resulting mixture was stirred at RT for 4 h and diluted with CH2Cl2. The organic solution was washed with H2O, dried over Na2SO4 and concentrated. The residue was purified by SiO2 chromatography to give N-[4-(isopropyl)phenyl]{2-methylthio-4-[(4-pyridylmethyl)amino]pyrimidin-5-yl}carboxamide. MS (ES+): 394 (M+H)+; (ES−): 392 (M−H)−. Calc'd C21H23N5OS−393.51.

Provenance & Evidence