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Crystal Structure of Ethyl 2,4-Dimethyl-1-phenyl-6-thioxo-1,6-dihydropyrimidine-5-carboxylate: The Product from the Reaction of Ethyl 3-Aminocrotonate, Phenylisothiocyanate and Acetic Anhydride

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Abstract

The crystal structure of ethyl 2,4-dimethyl-1-phenyl-6-thioxo-1,6-dihydropyrimidine-5-carboxylate (7) has been determined (monoclinic, P21/n, a 12.5543(9); b 7.6345(4); c 16.1568(14) Å, β 107.210(9)°) revealing a thioamide functional group instead of the thiazine ethyl (Z)-2,4-dimethyl-6-(phenylimino)-6H-1,3-thiazine-5-carboxylate (5) proposed previously. This has required the revision of the published structure for this multicomponent reaction which now has identified (7), not (5), as the product, supported by NMR and IR analysis.

Graphical Abstract

The crystal structure of the major product from the reaction of ethyl 3-aminocrotonate, phenylisothiocyanate and acetic anhydride is ethyl 2,4-dimethyl-1-phenyl-6-thioxo-1,6-dihydropyrimidine-5-carboxylate (shown), not the previously identified ethyl (Z)-2,4-dimethyl-6-(phenylimino)-6H-1,3-thiazine-5-carboxylate.

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Acknowledgements

The authors acknowledge the financial support of the Australian Research Council, the Australian Cancer Research and Ramaciotti Foundations.

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Authors and Affiliations

  1. Chemistry, School of Environmental and Life Sciences, University of Newcastle, Callaghan, NSW, 2308, Australia

    Peter J. Cossar, Cecilia C. Russell, Siobhann N. McCluskey, Dylan Pope & Adam McCluskey

  2. School of Chemistry and Molecular Biosciences, University of Queensland, Brisbane, QLD, 4072, Australia

    Paul V. Bernhardt

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  1. Peter J. Cossar
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  2. Cecilia C. Russell
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Correspondence to Adam McCluskey.

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Cossar, P.J., Russell, C.C., McCluskey, S.N. et al. Crystal Structure of Ethyl 2,4-Dimethyl-1-phenyl-6-thioxo-1,6-dihydropyrimidine-5-carboxylate: The Product from the Reaction of Ethyl 3-Aminocrotonate, Phenylisothiocyanate and Acetic Anhydride. J Chem Crystallogr 48, 91–95 (2018). https://doi.org/10.1007/s10870-018-0714-6

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