Verves E. Synthesis and properties of derivatives of pyrrolo[2,3-d] pyrimidine-6-carboxylic acid

Derivatives of pyrrolo[2,3-d]pyrimidine-6-carboxylic acid. The development of an approach to the synthesis of new derivatives of pyrrolo[2,3-d]pyrimidine-6-carboxylic acid, which contain 3-amino-2-hydroxypropyl substituents at the 7-position of heterocyclic ring. Organic synthesis, IR and NMR spectroscopy, chromato-mass-spectrometry, X-ray analysis. A number of pyrrolo[2,3-d]pyrimidine derivatives were synthesized via the cyclocondensation reaction of substituted 5-formyl-pyrimidine and ethyl esters of N-alkylglycines, using sodium methylate. A study on the bromolactonization reaction derivatives of 7-allyl-1H-pyrrolo[2,3-d]-pyrimidine-6-carboxylic acid made it possible to obtain reagents, that appeared to be promising for introduction of 3-amino-2-hydroxypropyl substituents to the 7-position of the heterocyclic ring. It was found that methyl ester of pyrrolo[2,3-d]pyrimidine-6-carboxylic acid, containing a 2,3-epoxypropyl substituent at the 7-position of heterocyclic ring in reaction with primary and secondary amines leads to the formation of new derivatives of pyrimido[5',4':4,5]pyrrolo[1,2-a]-[1,4]diazepine and pyrimido[5',4':4,5]pyrrolo[2,1-c][1,4]oxazine. Molecular docking of some derivatives of pyrrolo[2,3-d]pyrimidine-6-carboxylic acid was performed, and it's results indicate about perspectives of serching among them for effective inhibitors of protein kinases and adenosine receptor antagonists. Sphere of use - bioorganic chemistry