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

[ Vol. 17 , Issue. 1 ]

Author(s):

Vijay Kalhapure, Dhananjay Magar, Nishant Kothalkar, Tushar Khaladkar and Abhijit Roychowdhury*   Pages 23 - 28 ( 6 )

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.

Affiliation:

Savitribai Phule Pune University, Ganeshkind, Pune 411007, API R&D Centre, Emcure Pharmaceuticals Ltd., ITBT Park, Phase-II, MIDC, Hinjewadi, Pune 411057, API R&D Centre, Emcure Pharmaceuticals Ltd., ITBT Park, Phase-II, MIDC, Hinjewadi, Pune 411057, API R&D Centre, Emcure Pharmaceuticals Ltd., ITBT Park, Phase-II, MIDC, Hinjewadi, Pune 411057, Savitribai Phule Pune University, Ganeshkind, Pune 411007

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