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Henjum, Annika

Annika

Henjum

Presentation: 2026 ND EPSCoR Annual conference 

October 20, 2026, Minot, North Dakota

Rapid synthesis of N-[1-(4-pyrimidinyl)ethyl]formamide

Annika

Henjum

Undergraduate Student
Minot State University

Lioudmila I. Bobyleva, MS, Minot State University ; Mikhail M. Bobylev, PhD, Minot State University

Session

Poster #15

Background: Earlier, we developed a rapid procedure for the Leuckart reaction and successfully applied it for the synthesis of a series of substituted N-(1-phenylethyl)formamides. Depending on the type of substituent on the benzene ring, most of the reactions were completed in 10 to 20 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 the reaction can be completed even faster – in 2 minutes and 1 minute, 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 may proceed even faster than the reaction with 2-acetylpyrazine. In this work, the hypothesis as tested in the reaction between 4-acetylpyrimidine and formamide. Methods: The reaction was conducted on a 1 mmol scale at 180-196°C. Extraction and column chromatography were used for the isolation of the product. NMR spectroscopy and elemental analysis were used to determine the structure of the product. Results: The reaction was completed in 1 minutes. The isolated yield N-[1-(4-pyrimidinyl)ethyl]formamide was 86%. Conclusions: The results of the reaction is in agreement with the initial hypothesis. The reaction time of 4-acetylpyrimidine was as fast as 2-acetylpyrazine. 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 National Institute of General Medical Sciences and by the National Science Foundation under NSF EPSCoR Track-1 Cooperative Agreement OIA #1946202.

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