V. Kataev, S. A. Mesheryakova, E. S. Mesheryakova
May 1, 2021
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Journal
Russian Journal of General Chemistry
Abstract
The reaction of 6-methyluracil with 2-chloromethyltiiran affords 6-methyl-3-(thietan-3-yl)uracil. Its subsequent reaction with N-(2,6-dichlorophenyl)-2-chloroacetamide resulted in N-(2,4-dichlorophenyl)-2-[6-methyl-2,4-dioxo-3-(thietan-3-yl)-1,2,3,4-tetrahydropyrimidin-1-yl]acetamide, proved by X-ray analysis, NMR and IR spectroscopy. Computer modeling at the PBE/3ζ, PBE/cc-pVDZ and PBE/SV(P) levels showed that its conformational behavior is determined by internal rotation of the thietanyl group both in the gas phase and in chloroform or dimethyl sulfoxide solutions.