Category: pyrimidinesOn March 12, 1982, Barczynski, P.; Van der Plas, H. C. published an article in Journal of Organic Chemistry. The article was 《Ring transformations in reactions of heterocyclic compounds with nucleophiles. Part 24. Pyrimidines. Part 86. Conversion of 5-nitropyrimidine into 2-substituted 5-nitropyrimidine and 2-amino-5-nitropyridines by amidines》. The article mentions the following:
The reaction of 5-nitropyrimidine (I) with benzamidine, pivalamidine, acetamidine, propionamidine, α-phenylacetamidine, O-methylisourea hydrochlorides, and cyanamide in ethanolic solution in the presence of Et3N was investigated. I and alkyl(aryl)amidines, having no active methylene groups attached to the amidine moiety (pivalamidine, benzamidine), gave the corresponding 2-substituted 5-nitropyrimidines in good yields. With acetamidine and propionamidine, 2-amino-5-nitropyridines were also formed; with α-phenylacetamidine a 2-amino-5-nitropyridine derivative was obtained exclusively. The reaction of I with both O-methylisourea and cyanamide leads to 2-amino-5-nitropyrimidine. These reactions provide new examples of degenerate ring transformations of the pyrimidine ring system and of the ring transformation of pyrimidines into pyridines. After reading the article, we found that the author used 2-Methoxy-5-nitropyrimidine(cas: 14001-69-5Category: pyrimidines)
2-Methoxy-5-nitropyrimidine(cas: 14001-69-5) is a member of ether. When aromatic ethers are exposed to halogen in the presence or absence of a catalyst, they undergo halogenation, such as bromination.Category: pyrimidines
Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia