EFFECTIVE METHOD FOR PRODUCING 2-STYRYLPYRIMIDIN-4(3H)-ONES

A convenient scheme for the synthesis of a series of compounds of (E)-6-R-2-styryl­pyrimidin-(4H)-ones by reduction of 2-(2-oxo-2-arylethylidene)-2,3-dihydropyrimidin-4(1H)-ones with sodium borohydride was developed followed by dehydration of the obtained 2-(2-hydroxy-2-arylethyl)pyrimidin-­4(3H)-­ones in orthophosphoric acid at eleva­ted temperature. Two variants of modification of 2-styrylpyrimidin-4(3H)-ones are propo­sed. Namely, 4-methylbenzosulfonates were synthesized, and it was also established that upon the interaction of (E)-6-methyl-2-styrylpyrimidin-(4H)-one with an equimolecular amount of Br2, the reaction product turned out to be (E)-5-bromo-6-R-2-styrylpyrimidine-(4H)-­one. The structure of the synthesized compounds was established using NMR spectroscopy and mass spectrometry.