Reaction Scope of Methyl 1,2,3-Triazine-5-carboxylate with Amidines and the Impact of C4/C6 Substitution

Ryan E. Quiñones, Zhi-Chen Wu and Dale L. Boger*

*Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, United States, Email: dale.bogeroutlook.com

R. E. Quiñones, Z.-C. Wu, D. L. Boger, J. Org. Chem., 2021, 86, 13465-13474.

DOI: 10.1021/acs.joc.1c01553

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Abstract

Methyl 1,2,3-triazine-5-carboxylate reacts with alkyl and aryl amidines at room temperature at remarkable rates (<5 min, 0.1 M in CH₃CN) nearly 10000-fold faster than that of unsubstituted 1,2,3-triazine to provide product pyrimidines in high yields. C4 Methyl substitution of the 1,2,3-triazine had little effect on the rate of the reaction, whereas C4/C6 dimethyl substitution slowed the reaction.

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proposed pathways

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Key Words

pyrimidines

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ID: J42-Y2021