An Efficient Kilogram-Scale Synthesis of N,N′-Bis(4,6-disubstituted 1,3,5-triazin-2-yl)-4-aminophenetylamine

A practical large-scale synthesis was developed for the preparation of N,N′-bis(4,6-disubstituted 1,3,5-triazin-2-yl)-4-aminophenethylamine derivatives exemplified by compound 2. This route is a six-step procedure starting from commercially available cyanuric chloride and 3-(tert-butoxycarbonylamino) aniline based on the reactivity differences of the three chlorine atoms on the triazine ring. The optimized procedure was scaled up to give the final product 2 in an overall yield of 61% and 99.9% purity. These low-molecular weight compounds mimic the ability of protein A to bind to IgG antibody.