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Cyclisations and fragmentations in the alkylation of 6-chloro-5-hydroxy-4-aminopyrimidines with aminoalkyl chlorides

Lookup NU author(s): Edwige Picazo, Amy Heptinstall, Dr Celine CanoORCiD, Emeritus Professor Bernard Golding, Professor Mike Waring

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Abstract

Substituted aminopyrimidines are an important class of compounds, in part because they frequently show biological activity. Facile synthesis of polysubstituted aminopyrimidines is highly desirable for the synthesis of screening libraries. We describe a route to 4,6‐diamino‐5‐alkoxypyrimidines via a S_NAr‐alkylation‐S_NAr sequence from readily available 4,6‐dichloro‐5‐methoxypyrimidine, which allows the synthesis of such compounds with regiochemical control. Extension of this approach to alkylating agents bearing amino substituents led to unexpected and, in some cases, unprecedented products resulting from intramolecular S_NAr cyclisation and subsequent fragmentation.

Publication metadata

Author(s): Picazo EMH, Heptinstall AB, Wilson DM, Cano C, Golding BT, Waring MJ

Publication type: Article

Publication status: Published

Journal: Journal of Heterocyclic Chemistry

Year: 2021

Volume: 58

Issue: 4

Pages: 947-951

Print publication date: 01/04/2021

Online publication date: 16/01/2021

Acceptance date: 10/01/2021

Date deposited: 31/03/2021

ISSN (print): 0022-152X

ISSN (electronic): 1943-5193

Publisher: Wiley-Blackwell Publishing Ltd.

URL: https://doi.org/10.1002/jhet.4228

DOI: 10.1002/jhet.4228

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