A Simple and Easily Implemented Method for the Regioselective Introduction of Deuterium into Azolo[1,5- a]pyrimidines Molecules

Gevorg G Danagulyan; Henrik A Panosyan; Vache K Gharibyan; Ani H Hasratyan

doi:10.3390/molecules28062869

A Simple and Easily Implemented Method for the Regioselective Introduction of Deuterium into Azolo[1,5- a]pyrimidines Molecules

Molecules. 2023 Mar 22;28(6):2869. doi: 10.3390/molecules28062869.

Authors

Gevorg G Danagulyan^{1

2}, Henrik A Panosyan², Vache K Gharibyan¹, Ani H Hasratyan^{1

2}

Affiliations

¹ Laboratory of Bioactive Azaheterocycles, Institute of Biomedicine and Pharmacy, Russian-Armenian University, Hovsep Emin Str. 123, Yerevan 0051, Armenia.
² Scientific and Technological Center of Organic and Pharmaceutical Chemistry, The National Academy of Sciences of the Republic of Armenia, Azatutyan Ave. 26, Yerevan 0014, Armenia.

Abstract

A method for the technically easy-to-implement synthesis of deuterium-labeled pyrazolo[1,5-a]pyrimidines and 1,2,4-triazolo[1,5-a]pyrimidines have been developed. The regioselectivity of such transformations has been shown. ¹H NMR and mass spectrometric methods have proved the quantitative nature of such transformations and the kinetics of deuterium exchange has been studied. Spectrally, at different temperatures (+30 °C, -10 °C and -15 °C), the kinetics of the process was studied both in CD₃OD and in deuterated alkali.

Keywords: 1,2,4-triazolo[1,5-a]pyrimidine; H/D exchange; methylpyrimidines; pyrazolo[1,5-a]pyrimidine; regioselectivity.

Grants and funding

The study was funded by Russian-Armenian University (RAU).