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Synthesis and structural characterization of the 5-(2-haloethyl)pyrimidines – hydrogen-bonded chains in α-(1-carbamyliminomethylene)-γ-butyrolactone

Three novel 5-(2-haloethyl)pyrimidine derivatives were synthesized and characterized by 1H-NMR, 13C-NMR, MS, IR spectra and elemental analysis. Iodine and chlorine atoms in the C-5 side chain were introduced by reaction of 5-(2-hydroxyethyl)pyrimidine with hydroiodic acid and phosphoryl chloride, respectively. The structure of the intermediate  -(1-carbamyliminomethylene)- -butyrolactone was determined by X-ray crystal structure analysis. The molecule deviates very slightly from planarity. Three N H• • • O hydrogen bonds link the molecules into one-dimensional chains of edge-fused rings.

5-(2-haloethyl)pyrimidine ; synthesis ; X-ray crystal structure ; hydrogen bonds

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