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Synthesis 2023; 55(16): 2503-2516
DOI: 10.1055/a-2063-0303
paper

Regioselective Suzuki–Miyaura Reactions of Ethyl 2,6-Dibromo­pyrazolo[1,5-a]pyrimidine-3-carboxylate

Badr Jismy∗
a   Laboratoire de Physico-Chimie des Matériaux et des Electrolytes pour l’Energie (PCM2E), EA 6299, Faculté des Sciences et Techniques, Université de Tours, Avenue Monge Faculté des Sciences, Parc de Grandmont, 37200 Tours, France
,
Chaima Messaoudi
a   Laboratoire de Physico-Chimie des Matériaux et des Electrolytes pour l’Energie (PCM2E), EA 6299, Faculté des Sciences et Techniques, Université de Tours, Avenue Monge Faculté des Sciences, Parc de Grandmont, 37200 Tours, France
b   Laboratoire de Synthese Organique Sélective et Hétérocyclique – Evaluation de l’Activité Biologique, Faculté des Sciences de Tunis, Université de Tunis El Manar, Tunis 2092, Tunisia
,
Hassan Allouchi
c   Faculté de Pharmacie, Université de Tours, EA 7502 SIMBA, 31 Avenue Monge, 37200 Tours, France
,
Abdellatif Tikad
d   Laboratoire de Chimie Moléculaire et Substances Naturelles, Faculté des Sciences, Université Moulay Ismail, B.P. 11201, Zitoune, Meknès, Morocco
,
Hédi M’Rabet
b   Laboratoire de Synthese Organique Sélective et Hétérocyclique – Evaluation de l’Activité Biologique, Faculté des Sciences de Tunis, Université de Tunis El Manar, Tunis 2092, Tunisia
,
Mohamed Abarbri∗
a   Laboratoire de Physico-Chimie des Matériaux et des Electrolytes pour l’Energie (PCM2E), EA 6299, Faculté des Sciences et Techniques, Université de Tours, Avenue Monge Faculté des Sciences, Parc de Grandmont, 37200 Tours, France
› Author AffiliationsThis research received no external funding.
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Abstract

A variety of novel disubstituted pyrazolo[1,5-a]pyrimidine derivatives have been prepared via sequential site-selective cross-coupling reactions of ethyl 2,6-dibromopyrazolo[1,5-a]pyrimidine-3-carboxylate. The regiocontrolled Suzuki–Miyaura reaction proceeded with excellent selectivity in favor of position C6 after careful optimization of the cross-coupling conditions. The monobrominated compounds, obtained on a large scale, were subjected to a second arylation, alkynylation or amination, leading to a new series of ethyl 2,6-disubstituted pyrazolo[1,5-a]pyrimidine-3-carboxylates. These results constitute an efficient regioselective approach for diversification of the chemically and biologically interesting pyrazolo[1,5-a]pyrimidine heterocycle at C2 and C6 positions.

Key words

site-selective cross-coupling reaction - pyrazolo[1,5-a]pyrimidine - Suzuki–Miyaura reaction - arylation - alkynylation - amination

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2063-0303.
  • Supporting Information


Publication History

Received: 16 February 2023

Accepted after revision: 27 March 2023

Accepted Manuscript online:
27 March 2023

Article published online:
24 April 2023

© 2023. Thieme. All rights reserved

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