Improved synthesis, spectral characteristics and spatial structure of ethyl 2-hydroxy-8-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxylate

Authors

  • I. V. Ukrainets National University of Pharmacy, Ukraine
  • N. L. Bereznyakova National University of Pharmacy, Ukraine
  • K. A. Taran National University of Pharmacy, Ukraine
  • O. O. Davidenko National Pirogov Memorial Medical University, Ukraine

DOI:

https://doi.org/10.24959/ophcj.14.800

Keywords:

heterocyclic tricarbonylmethane derivatives, 2-aminopyridines, esters, 2-hydroxy-4-oxo-4H-pyrido[ 1, 2-a]pyrimidine-3-carboxylic acids

Abstract

The improved method for obtaining ethyl 2-hydroxy-8-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxylate being of interest as a base for synthesis of antiviral medicines has been suggested. The method involves a gradual addition of the solution of 2-amino-4-methylpyridine in triethylmethanetricarboxylate used as an acylating and condensing agent, as well as a high boiling heating agent simultaneously in the excess of triethylmethanetricarboxylate preheated to 150°C. This modification allows not only to reduce considerably regeneration of triethylmethanetricarboxylate taken in excess, but practically to avoid completely the undesirable formation of by-product – 2-hydroxy-8-methyl-N-(4-methypyridin-2-yl)-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxamide. It has been found by X-ray diffraction analysis that in the crystal the ethyl 2-hydroxy-8-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxylate synthesized exists in the zwitterionic form with localization of the positive charge at the protonated nitrogen atom and the negative charge at the carbon atom in position 3 of the pyridopyrimidine ring. Based on the study of NMR 1H and 13C spectra the assumption that the test compound exits as an equilibrium mixture of two tautomeric forms in solution has been expressed.

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Published

2014-09-12

How to Cite

(1)
Ukrainets, I. V.; Bereznyakova, N. L.; Taran, K. A.; Davidenko, O. O. Improved Synthesis, Spectral Characteristics and Spatial Structure of Ethyl 2-Hydroxy-8-Methyl-4-Oxo-4H-pyrido[1,2-a]pyrimidine-3-Carboxylate. J. Org. Pharm. Chem. 2014, 12, 23-27.

Issue

Vol. 12 No. 3(47) (2014)

Section

Original Researches

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