Diisopropylethylamine → Ethyl 4'-methyl-5-((2-methylpyrimidin-5-yl)methylcarbamoyl)biphenyl-3-carboxylate

Participants

Reaction Steps

To a mixture of crude 5-(ethoxycarbonyl)-4′-methylbiphenyl-3-carboxylic acid (450 mg, 1.6 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (610 mg, 3.2 mmol), 1-hydroxybenzotriazole hydrate (240 mg, 1.6 mmol), CH2Cl2 (5 mL) were added (2-methylpyrimidin-5-yl)methanamine (290 mg, 2.4 mmol) and N,N-diisopropylethylamine (0.41 mL, 2.4 mmol). The reaction mixture was stirred at room temperature overnight, and then diluted with aq. NaHCO3 solution and EtOAc (100 mL). The organic layer was separated, washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The residue was purified by silica gel column (0-20% MeOH/CH2Cl2) to afford the title product as a white foam.

Provenance & Evidence