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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2024-11-01
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| author | Aleksandr V. Dambaev Denis A. Kolesnik Igor P. Yakovlev Tamara L. Semakova |
| author_facet | Aleksandr V. Dambaev Denis A. Kolesnik Igor P. Yakovlev Tamara L. Semakova |
| author_sort | Aleksandr V. Dambaev |
| collection | DOAJ |
| description | 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. |
| format | Article |
| id | doaj-art-398b3d07c2b246439cbadc1dee4b70eb |
| institution | Kabale University |
| issn | 2673-4583 |
| language | English |
| publishDate | 2024-11-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Chemistry Proceedings |
| spelling | doaj-art-398b3d07c2b246439cbadc1dee4b70eb2025-08-20T03:26:20ZengMDPI AGChemistry Proceedings2673-45832024-11-0116110410.3390/ecsoc-28-20128Formylation of 2-Methylpyrimidine-4,6-diol Under the Conditions of the Vilsmeier–Haack ReactionAleksandr V. Dambaev0Denis A. Kolesnik1Igor P. Yakovlev2Tamara L. Semakova3State Federal-Funded Educational Institution of Higher Education, Saint Petersburg State Chemical and Pharmaceutical University, Ministry of Healthcare of the Russian Federation, Professor Popov Str., 14, Lit. A, St. Petersburg 197022, RussiaState Federal-Funded Educational Institution of Higher Education, Saint Petersburg State Chemical and Pharmaceutical University, Ministry of Healthcare of the Russian Federation, Professor Popov Str., 14, Lit. A, St. Petersburg 197022, RussiaState Federal-Funded Educational Institution of Higher Education, Saint Petersburg State Chemical and Pharmaceutical University, Ministry of Healthcare of the Russian Federation, Professor Popov Str., 14, Lit. A, St. Petersburg 197022, RussiaState Federal-Funded Educational Institution of Higher Education, Saint Petersburg State Chemical and Pharmaceutical University, Ministry of Healthcare of the Russian Federation, Professor Popov Str., 14, Lit. A, St. Petersburg 197022, RussiaIn 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.https://www.mdpi.com/2673-4583/16/1/104formylationpyrimidine-4,6-diolsVilsmeier–Haack reactionelectrophilic substitution |
| spellingShingle | Aleksandr V. Dambaev Denis A. Kolesnik Igor P. Yakovlev Tamara L. Semakova Formylation of 2-Methylpyrimidine-4,6-diol Under the Conditions of the Vilsmeier–Haack Reaction Chemistry Proceedings formylation pyrimidine-4,6-diols Vilsmeier–Haack reaction electrophilic substitution |
| title | Formylation of 2-Methylpyrimidine-4,6-diol Under the Conditions of the Vilsmeier–Haack Reaction |
| title_full | Formylation of 2-Methylpyrimidine-4,6-diol Under the Conditions of the Vilsmeier–Haack Reaction |
| title_fullStr | Formylation of 2-Methylpyrimidine-4,6-diol Under the Conditions of the Vilsmeier–Haack Reaction |
| title_full_unstemmed | Formylation of 2-Methylpyrimidine-4,6-diol Under the Conditions of the Vilsmeier–Haack Reaction |
| title_short | Formylation of 2-Methylpyrimidine-4,6-diol Under the Conditions of the Vilsmeier–Haack Reaction |
| title_sort | formylation of 2 methylpyrimidine 4 6 diol under the conditions of the vilsmeier haack reaction |
| topic | formylation pyrimidine-4,6-diols Vilsmeier–Haack reaction electrophilic substitution |
| url | https://www.mdpi.com/2673-4583/16/1/104 |
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