Abstract
The methylation of dihydropyrimidinylidenecyanoacetic esters by various methylating reagents leads to better yields when anions of ylidene derivatives of pyrimidine are used. The structure of the products of N- and C-methylation formed and their ratio were established with the aid of the IR and UV spectra and by 1H and 13C NMR spectroscopy. The product of C-methylation contains a methyl group at the C(7) atom of the side chain, while the product of N-methylation contains a methyl group at the nitrogen atom of the pyrimidine ring. For 6-ylidene derivatives, N-methylation occurs at the heterocyclic atom distant from the tautomerizing chain. For 2-and 6-ylidene derivatives of pyrimidine, the ratio of the products of N- and C-methylation can be changed by varying the alkylating reagent.
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For communication 1, see [1].
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1537–1543, November, 1984.
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Zagulyaeva, O.A., Grigorkina, O.A., Mamatyuk, V.I. et al. Chemical properties of ylidene derivatives of azines. 2. The methylation of dihydropyrimidinylidenecyanoacetic esters and their anions. Chem Heterocycl Compd 20, 1270–1275 (1984). https://doi.org/10.1007/BF00505721
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DOI: https://doi.org/10.1007/BF00505721