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Short Paper | Regular issue | Vol 92, No. 12, 2016, pp.2271-2277
Published online, 8th November, 2016
DOI: 10.3987/COM-16-13592
Regioselective Bromination of 2-Iodomethyl-2,3-Dihydrothiazolo[3,2-a]pyrimidin-5-one

Renata Studzińska,* Renata Kołodziejska, Tomasz Kosmalski, and Bożena Modzelewska-Banachiewicz

*Department of Organic Chemistry, Nicolaus Copernicus University, Collegium Medicum in Bydgoszcz, Jurasza 2, Bydgoszcz 85-089, Poland

Abstract

The bromination reactions of 2-iodomethyl-2,3- dihydrothiazolo[3,2-a]pyrimidin-5-one were carried out using bromine and NBS as the brominating agent. Depending on the brominating agent used and a solvent two bromo derivatives were obtained: the product of electrophilic substitution in the pyrimidin ring and the product containing two bromine atoms which was formed as a result of two parallel reactions – an electrophilic substitution on the pyrimidine ring and a nucleophilic substitution of iodine. The position of bromine atoms in the obtained compounds was confirmed using 1H NMR spectrum.