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Current Organic Synthesis

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ISSN (Print): 1570-1794
ISSN (Online): 1875-6271

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Letter Article

Synthesis of Substituted imidazo [1, 5-a] pyrimidine-2-(1H)-one Core Structure

Author(s): Vijay Kalhapure, Dhananjay Magar, Nishant Kothalkar, Tushar Khaladkar and Abhijit Roychowdhury*

Volume 17, Issue 1, 2020

Page: [23 - 28] Pages: 6

DOI: 10.2174/1389200220666191122103445

Price: $65

Abstract

Background and Objective: The objective of our work was to establish a facile and scalable synthesis of imidazopyridone for further use in medicinal chemistry applications. An easy synthesis of a core scaffold will enable the medicinal chemistry community to use imidazopyridone as a privileged scaffold in new chemical entity (NCE) synthesis.

Materials and Methods: The synthesis was achieved from commercially available and cheap raw materials like amino acetonitrile hydrochloride or commercially available guanidine.

Results: Simple transformation starting from amino acetonitrile hydrochloride leads to the synthesis of a versatile imidazo [1, 5-a] pyrimidine-2-(1H)-one core structure. Using suitable functionalized starting materials, a set of NCEs were synthesized to demonstrate the application of the developed synthetic scheme. Similarly, guanidine was also used to synthesize a regioisomer of imidazopyridone in moderate to good yields.

Conclusion: We demonstrate the synthesis of two different regio-isomers of imidazopyrimidinone using simple chemical transformations. Its application in synthesizing NCEs has also been exhibited in the present work.

Keywords: Imidazole, imidazo-pyrimidones, amino acetonitrile, heterocycles, New Chemical Entity (NCE) synthesis, medicinal chemistry.

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