Phenoxide leaving group SNAr strategy for the facile preparation of 7-amino-3-aryl pyrazolo[1,5-a]pyrimidines from a 3-bromo-7-phenoxypyrazolo[1,5-a]pyrimidine intermediate

John G. Catalano; Vishwanath Gaitonde; Mallesh Beesu; Anna L. Leivers; J. Brad Shotwell

doi:10.1016/j.tetlet.2015.09.068

Phenoxide leaving group S_NAr strategy for the facile preparation of 7-amino-3-aryl pyrazolo[1,5-a]pyrimidines from a 3-bromo-7-phenoxypyrazolo[1,5-a]pyrimidine intermediate

John G. Catalano
, Vishwanath Gaitonde
, Mallesh Beesu
, Anna L. Leivers
, J. Brad Shotwell

Medicinal Chemistry

Research output: Contribution to journal › Article › peer-review

9 Scopus citations

Abstract

We have discovered a 3-bromo-7-phenoxypyrazolo[1,5-a]pyrimidine intermediate that allows for the direct sequential funtionalization of the 3-position and 7-position of a pyrazolo[1,5-a]pyrimidine scaffold. The intermediate and general method described herein offer an improvement over prior methods, particularly in cases where multiple unique 3-aryl substituents are to be incorporated in conjunction with multiple unique 7-amino substituents.

Original language	English (US)
Pages (from-to)	6077-6079
Number of pages	3
Journal	Tetrahedron Letters
Volume	56
Issue number	44
DOIs	https://doi.org/10.1016/j.tetlet.2015.09.068
State	Published - Oct 28 2015

Bibliographical note

Funding Information:
The authors wish to acknowledge the members of the Antiviral Discovery Performance Unit, as well as the Analytical and Separations groups at GlaxoSmithKline for their support and camaraderie. This work was financially supported by GlaxoSmithKline.

Publisher Copyright:
© 2015 Elsevier Ltd. All rights reserved.

Keywords

Heterocycle
Phenoxide
Pyrazolo[1,5-a]pyrimidine
SNAr
Suzuki

Publisher link

10.1016/j.tetlet.2015.09.068

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Phenoxide leaving group S_NAr strategy for the facile preparation of 7-amino-3-aryl pyrazolo[1,5-a]pyrimidines from a 3-bromo-7-phenoxypyrazolo[1,5-a]pyrimidine intermediate. / Catalano, John G.; Gaitonde, Vishwanath; Beesu, Mallesh et al.
In: Tetrahedron Letters, Vol. 56, No. 44, 28.10.2015, p. 6077-6079.

Research output: Contribution to journal › Article › peer-review

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title = "Phenoxide leaving group SNAr strategy for the facile preparation of 7-amino-3-aryl pyrazolo[1,5-a]pyrimidines from a 3-bromo-7-phenoxypyrazolo[1,5-a]pyrimidine intermediate",

abstract = "We have discovered a 3-bromo-7-phenoxypyrazolo[1,5-a]pyrimidine intermediate that allows for the direct sequential funtionalization of the 3-position and 7-position of a pyrazolo[1,5-a]pyrimidine scaffold. The intermediate and general method described herein offer an improvement over prior methods, particularly in cases where multiple unique 3-aryl substituents are to be incorporated in conjunction with multiple unique 7-amino substituents.",

keywords = "Heterocycle, Phenoxide, Pyrazolo[1,5-a]pyrimidine, SNAr, Suzuki",

author = "Catalano, \{John G.\} and Vishwanath Gaitonde and Mallesh Beesu and Leivers, \{Anna L.\} and Shotwell, \{J. Brad\}",

note = "Funding Information: The authors wish to acknowledge the members of the Antiviral Discovery Performance Unit, as well as the Analytical and Separations groups at GlaxoSmithKline for their support and camaraderie. This work was financially supported by GlaxoSmithKline. Publisher Copyright: {\textcopyright} 2015 Elsevier Ltd. All rights reserved.",

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AU - Catalano, John G.

AU - Gaitonde, Vishwanath

AU - Beesu, Mallesh

AU - Leivers, Anna L.

AU - Shotwell, J. Brad

N1 - Funding Information: The authors wish to acknowledge the members of the Antiviral Discovery Performance Unit, as well as the Analytical and Separations groups at GlaxoSmithKline for their support and camaraderie. This work was financially supported by GlaxoSmithKline. Publisher Copyright: © 2015 Elsevier Ltd. All rights reserved.

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N2 - We have discovered a 3-bromo-7-phenoxypyrazolo[1,5-a]pyrimidine intermediate that allows for the direct sequential funtionalization of the 3-position and 7-position of a pyrazolo[1,5-a]pyrimidine scaffold. The intermediate and general method described herein offer an improvement over prior methods, particularly in cases where multiple unique 3-aryl substituents are to be incorporated in conjunction with multiple unique 7-amino substituents.

AB - We have discovered a 3-bromo-7-phenoxypyrazolo[1,5-a]pyrimidine intermediate that allows for the direct sequential funtionalization of the 3-position and 7-position of a pyrazolo[1,5-a]pyrimidine scaffold. The intermediate and general method described herein offer an improvement over prior methods, particularly in cases where multiple unique 3-aryl substituents are to be incorporated in conjunction with multiple unique 7-amino substituents.

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KW - Phenoxide

KW - Pyrazolo[1,5-a]pyrimidine

KW - SNAr

KW - Suzuki

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