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Paper | Regular issue | Vol 26, No. 11, 1987, pp.2905-2910
Published online, 1st January, 1970
DOI: 10.3987/R-1987-11-2905
The Regioselectivity of Amination of Certain 4-Dimethylaminopyridines

Michael P. Groziak and Laura M. Melcher

*Roger Adams Laboratory, School of Chemical Sciences, University of Illinois, 1209 West California Street, Urbana, IL 61801-3731, U.S.A.

Abstract

Under the homogeneous aminating conditions of KNH2 in NH3, 3-bromo-4-dimethylaminopyridine 2 affords a mixture of 2-amino-5-bromo-4-dimethylaminopyridine 3 and 3-amino-4-dimethylaminopyridine 4, along with the product of debrominatian, 4-dimethylaminopyridine 1. Compound 3 was debrominated with Zn in HOAc to afford 2-amino-4-dimethylaminopyridine 5. The regioselectivity observed for the homogeneous amnation of 2 is precisely that predicted by an analysis of the lowest unoccupied frontier molecular orbital coefficients.