Bobylev, Mikhail
Mikhail
Bobylev
Presentation: 2026 ND EPSCoR Annual conference
October 20, 2026, Minot, North Dakota
Rapid synthesis of N-ethyl-N-[1-(4-pyrimidinyl)ethyl]formamide
Mikhail
Bobylev
Faculty Member
Minot State University
Mason Lemer, UG Student Minot State University; Lioudmila I. Bobyleva, MS, Minot State University ; ; ;
Session
Poster #8
Background: Earlier, we developed a rapid procedure for the Leuckart reaction and successfully applied it for the synthesis of a series of substituted N-ethyl-(1-phenylethyl)formamides. Depending on the type of substituent on the benzene ring of the starting acetophenone, most of the reactions were completed in 30 to 50 minutes, which is much faster than the traditional Leuckart reaction that is usually completed within 3 to 6 hours. Recently, we extended our investigation to acetylpyridines and 2-acetylpyrazine, which showed the reaction can be completed even faster – in 15 and 9 minutes, respectively. Hypothesis: 4-acetylpyrimidine and 2-acetylpyrazine are close analogs. The 1,3 position of nitrogen atoms in the pyrimidine ring may provide even stronger electron-withdrawing action compared to the 1,4 position in the pyrazine ring. The stronger electron-withdrawing action should make the adjacent carbonyl more electrophilic, resulting in a faster reaction. Consequently, the reaction with 4-acetylpyrimidine should proceed faster than the reaction with 2-acetylpyrazine. In this work, the hypothesis is tested in the reaction between 4-acetylpyrimidine and N-ethylformamide. Methods: The reaction was conducted on a 5 mmol scale at 180-186°C. Extraction and column chromatography were used for the isolation of the product of the reaction. NMR spectroscopy and elemental analysis were used to determine the structure of the product. Result: The reaction was completed in 3 minutes. The isolated yield N-ethyl-N-[1-(4-pyrimidinyl)ethyl]formamide was 56%. Conclusion: The results of the reaction support the initial hypothesis. The reaction time of 4-acetylpyridene was faster than the reaction time of 2-acetylpyrazine. N-ethyl-N-[1-(4-pyrimidinyl)ethyl]formamide is a new compound. Support: Research presented in this presentation was supported by NIH Grant 8 P20 GM103442-12 from the NIGMS and by the NSF under NSF EPSCoR Track-1 Cooperative Agreement OIA #1946202.
