Вивчення взаємодії 4,6-дихлоропіримідин-5-карбальдегіду з естерами гліцину

• Date: 2018
• Main Authors: Zinchenko, H. M., Muzychka, L. V., Biletskiy, I. I., Smolii, O. B.
• Format: Article
• Language: Ukrainian
• Published: National University of Pharmacy 2018
• Subjects: 4; 6-дихлоропіримідин-5-карбальдегід; піридо[2; 3-d]піримідин-7-они; піроло[2; 3-d]піримідини; циклізація; УДК 547.828 547.824
• Online Access: https://ophcj.nuph.edu.ua/article/view/ophcj.18.935
• Journal Title: Journal of Organic and Pharmaceutical Chemistry

Aim. To study the interaction of 4,6-dichloropyrimidine-5-carbaldehyde with methyl- and with tert-butylglycinate depending on the reaction conditions.Results and discussion. It has been found that the reaction of 4,6-dichloro-5-formylpyrimidine with hydrochlorides of glycine esters in the presence of triethylamine leads to obtaining derivatives of N-(5-formylpyrimidin-4-yl)glycinate and cyclization products: pyrrolo[2,3-d]pyrimidine and pyrido[2,3-d]pyrimidine.Experimental part. The interaction of 4,6-dichloropyrimidine-5-carbaldehyde with methyl or tert-butyl glycinate in methanol in the presence of triethylamine depending on the molar ratio gives the mixture of 5-hydroxy-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine and 6-amino-4-chloro-7-oxopyrido[2,3-d]pyrimidine-8(7H)-yl)acetate.The composition and structure of the compounds synthesized have been confirmed by NMR-spectroscopy, chromatography mass-spectrometry and elemental analysis.Conclusions. The previously unknown derivatives of pyrrolo[2,3-d]pyrimidine and pyrido[2,3-d]pyrimidine have been obtained as a result of the interaction of 4,6-dichloro-5-formylpyrimidine with methyl and tert-butylglycinate.The reaction features depending on the reactants ratio have been studied. The prospects for the synthesis of potential biologically active compounds from 6-amino-4-chloro-7-oxopyrido[2,3-d]pyrimidine-8(7H)-yl)acetate have been described.