Unusual Nucleophilic Addition of Grignard Reagents in the Synthesis of 4-Amino-pyrimidines

Tinson, Ryan A. J., Hughes, David L., Ward, Leanne and Stephenson, G. Richard (2018) Unusual Nucleophilic Addition of Grignard Reagents in the Synthesis of 4-Amino-pyrimidines. ACS Omega, 3 (8). pp. 8937-8944.

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Abstract

Pyrimidines have always received considerable attention because of their importance in synthesis and elucidation of biochemical roles, in particular that of vitamin B1. Herein, we describe a reaction pathway in a Grignard reagent-based synthesis of substituted pyrimidines. A general synthesis of α-keto-2-methyl-4-amino pyrimidines and their C6-substituted analogues from 4-amino-5-cyano-2-methylpyrimidine is reported. The presence of the nitrile substituent in the starting material also results in an unusual reaction pathway leading to C6-substituted 1,2-dihydropyrimidines. Grignard reagents that give normal pyrimidine products under standard reaction conditions can be 14 switched to give dihydropyrimidines by holding the reaction at 0 °C before quenching.

Item Type: Article
Uncontrolled Keywords: pyrimidines,regioselectivity,grignard-reagents,chemistry(all) ,/dk/atira/pure/subjectarea/asjc/1600
Faculty \ School: Faculty of Science > School of Chemistry
Depositing User: LivePure Connector
Date Deposited: 15 Aug 2018 14:30
Last Modified: 01 Sep 2020 23:50
URI: https://ueaeprints.uea.ac.uk/id/eprint/68054
DOI: 10.1021/acsomega.8b01137

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