Formylation of 2-Methylpyrimidine-4,6-diol Under the Conditions of the Vilsmeier–Haack Reaction

In the course of this work, we explored the influence of the conditions of the Vilsmeier–Haack reaction for 2-methylpyrimidine-4,6-diol (<b>1</b>). We conducted a comparative analysis of approaches using various solvents (o-xylene, N,N-dimethylformamide (DMF), benzene, and dichloroethane...

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Main Authors: Aleksandr V. Dambaev, Denis A. Kolesnik, Igor P. Yakovlev, Tamara L. Semakova
Format: Article
Language:English
Published: MDPI AG 2024-11-01
Series:Chemistry Proceedings
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Online Access:https://www.mdpi.com/2673-4583/16/1/104
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Summary:In the course of this work, we explored the influence of the conditions of the Vilsmeier–Haack reaction for 2-methylpyrimidine-4,6-diol (<b>1</b>). We conducted a comparative analysis of approaches using various solvents (o-xylene, N,N-dimethylformamide (DMF), benzene, and dichloroethane) as the reaction medium, and the optimal one was selected. During the formylation of substrate 1 in these conditions, only 4,6-dihydroxy-2-methylpyrimidine-5-carbaldehyde (<b>2</b>) was successful. It should be noted that there was no substitution of hydroxyl groups for chlorine atoms observed in reactions with similar substrates. The structure of the resulting product <b>2</b> was proven using NMR spectroscopy on <sup>1</sup>H and <sup>13</sup>C nuclei and by mass spectrometry.
ISSN:2673-4583