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

Peter J. Cossar; Cecilia C. Russell; Siobhann N. McCluskey; Dylan Pope; Paul V. Bernhardt; Adam McCluskey

doi:10.1007/s10870-018-0714-6

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

Peter J. Cossar, Cecilia C. Russell, Siobhann N. McCluskey, Dylan Pope, Paul V. Bernhardt, Adam McCluskey (Lead / Corresponding author)

Centre for Targeted Protein Degradation

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

2 Citations (Scopus)

Abstract

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. [Figure not available: see fulltext.].

Original language	English
Pages (from-to)	91-95
Number of pages	5
Journal	Journal of Chemical Crystallography
Volume	48
Issue number	3
Early online date	22 May 2018
DOIs	https://doi.org/10.1007/s10870-018-0714-6
Publication status	Published - Sept 2018

Keywords

Dihydropyrimidine
Multicomponent reaction
Structure revision
Thiazine

ASJC Scopus subject areas

General Chemistry
Condensed Matter Physics

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10.1007/s10870-018-0714-6

Cite this

Cossar, P. J., Russell, C. C., McCluskey, S. N., Pope, D., Bernhardt, P. V., & McCluskey, A. (2018). 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. Journal of Chemical Crystallography, 48(3), 91-95. https://doi.org/10.1007/s10870-018-0714-6

@article{8336354e8d4c49a0ac38e8e7939807d5,

title = "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",

abstract = "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) {\AA}, 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. [Figure not available: see fulltext.].",

keywords = "Dihydropyrimidine, Multicomponent reaction, Structure revision, Thiazine",

author = "Cossar, {Peter J.} and Russell, {Cecilia C.} and McCluskey, {Siobhann N.} and Dylan Pope and Bernhardt, {Paul V.} and Adam McCluskey",

note = "Publisher Copyright: {\textcopyright} 2018, Springer Science+Business Media, LLC, part of Springer Nature.",

year = "2018",

month = sep,

doi = "10.1007/s10870-018-0714-6",

language = "English",

volume = "48",

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Cossar, PJ, Russell, CC, McCluskey, SN, Pope, D, Bernhardt, PV & McCluskey, A 2018, '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', Journal of Chemical Crystallography, vol. 48, no. 3, pp. 91-95. https://doi.org/10.1007/s10870-018-0714-6

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. / Cossar, Peter J.; Russell, Cecilia C.; McCluskey, Siobhann N. et al.
In: Journal of Chemical Crystallography, Vol. 48, No. 3, 09.2018, p. 91-95.

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

TY - JOUR

T1 - Crystal Structure of Ethyl 2,4-Dimethyl-1-phenyl-6-thioxo-1,6-dihydropyrimidine-5-carboxylate

T2 - The Product from the Reaction of Ethyl 3-Aminocrotonate, Phenylisothiocyanate and Acetic Anhydride

AU - Cossar, Peter J.

AU - Russell, Cecilia C.

AU - McCluskey, Siobhann N.

AU - Pope, Dylan

AU - Bernhardt, Paul V.

AU - McCluskey, Adam

PY - 2018/9

Y1 - 2018/9

N2 - 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. [Figure not available: see fulltext.].

AB - 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. [Figure not available: see fulltext.].

KW - Dihydropyrimidine

KW - Multicomponent reaction

KW - Structure revision

KW - Thiazine

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U2 - 10.1007/s10870-018-0714-6

DO - 10.1007/s10870-018-0714-6

M3 - Article

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SN - 1074-1542

VL - 48

SP - 91

EP - 95

JO - Journal of Chemical Crystallography

JF - Journal of Chemical Crystallography

IS - 3

ER -

Cossar PJ, Russell CC, McCluskey SN, Pope D, Bernhardt PV, McCluskey A. 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. Journal of Chemical Crystallography. 2018 Sept;48(3):91-95. Epub 2018 May 22. doi: 10.1007/s10870-018-0714-6

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

Abstract

Keywords

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