Diisopropylethylamine → N,N-Bis(4-methoxybenzyl)-4-(2-(6-methoxypyridin-3-ylamino)phenyl)-6-methyl-1,3,5-triazin-2-amine

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Reaction Steps

A mixture of 4-(2-aminophenyl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine (0.54 g, 1.22 mmol), copper acetate (0.33 g, 1.83 mmol, Aldrich, St. Louis, Mo.), 6-methoxypyridin-3-ylboronic acid (0.56 g mg, 3.67 mmol, Boron Molecular, Research Triangle Park, N.C.) and diisopropylethylamine (0.85 mL, 4.89 mmol) in DCM (15 mL) was stirred at room temperature for 16 h, filtered through a pad of Celite® (diatomaceous earth), and the solvent was removed in vacuo. The crude material was adsorbed onto silica gel and purified by chromatography through a Redi-Sep pre-packed silica gel column (40 g) eluting with a gradient of 0% to 2% 2 M NH3.MeOH in CH2Cl2, to give the title compound as a dark yellow oil. m/z (ESI, +ve ion) 548.8 (M+H)+.

Provenance & Evidence