In this work the alkylation of pyrimidine-2(1H)-thiones and -pyrimidinones with -bromomethyl-o-carborane was investigated. Deprotonated substituted pyrimidine-2(1H)-thiones, are known as the strong nucleophiles and very weak bases. Bromomethyl-o-carboranes are among the easiest prepared starting material for the synthesis of functionally substituted carboranes. So far, only the elekctrophilic substitution of bromine atom by metals (e.g., Mg, Li) was used in the synthetic ways starting from these compounds. Moreover, it was reported that the reactions of bromo- and chloromethyl-o-carboranes with variuos nucleophiles (Na2S/EtOH, NaI/acetone, potassium phthalimide/DMF) do not take place and result in the recovering of starting materials.

So it was found that 4,6-dimethylpyrimidine-2(1H)-thione reacts with -bromomethyl-o-carborane in DMF in the presence of triethylamine giving novel novel closo-2-(1-o-carboranylmethylsulfanyl)-4,6-dimethylpyrimidine. Carborane cage was destroyed at high temperature or in the alkaline conditions.

The structure of synthesized compounds was confirmed by the data of IR, UV, 1H, 13C and 11B NMR spectra.

Raktažodžiai: o-Carborane, BNCT, Pyrimidine derivatives