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Communication | Regular issue | Vol 57, No. 4, 2002, pp.615-621
Published online, 1st January, 1970
DOI: 10.3987/COM-02-9440
Synthesis, ESI and FAB Mass Spectrometry, and X-Ray Analysis of Di- and Tricationic Pyridinium Substituted Pyrimidines

Andreas Schmidt,* Pirjo Vainiotalo, Markus Karl Kindermann, and Martin Nieger

*Institut für Organische Chemie, Technische Universität Clausthal, Leibnizstrasse 6, D-38678 Clausthal-Zellerfeld, Germany

Abstract

Reaction of trichloropyrimidine (5) with 4-(dimethylamino)pyridine or 4-(pyrrolidin-1-yl)pyridine in ethyl acetate in the presence of sodium tetraphenylborate yielded the tricationic pyrimidines (7) and (8). Applying the same reaction conditions to tetrachloropyrimidine (6) resulted in the formation of highly reactive 5-chloro substituted trications (9) and (10), which could be intercepted by anhydrous alcohols to give the dicationic species (11) and (12). Characterizations by means of ESIMS and FABMS, a semiempirical calculation and an X-Ray analysis were performed.