The interaction of methyl anthranilate with N-(4,6-dimethylpyrimidin-2-yl)cyanamide, according to quantum-chemical calculations, X-ray diffraction, and spectral characteristics of a product obtained, leads exclusively to 2-[(4,6-dimethylpyrimidin-2-yl)amino]quinazolin-4(3H)-one and not to its isomer 2-amino-3-(4,6-dimethylpyrimidin-2-yl)quinazolin-4(3H)-one.
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J. H. Maguire and R. I. McKee, J. Org. Chem., 39, 3434 (1974).
Kh. S. Shikhaliev, A. S. Shestakov, S. M. Medvedeva, and N. V. Gusakova, Izv. Akad. Nauk., Ser. Khim., 164 (2008).
R. J. Grout and M. W. Partridge, J. Chem. Soc., 3540 (1960).
D. D. Nekrasov, Khim. Geterotsikl. Soed., 1283 (2004). [Chem. Heterocycl. Comp., 40, 1107 (2004)].
Kh. S. Shikhaliev, D. V. Kryl’skii, A. S. Shestakov, and A. V. Falaleev, Zh. Obshch. Khim., 73, 1216 (2003).
M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, T. Vreven, Jr., J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nalatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cros, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, M. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck. K. Paghavachari, J. D. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komafomi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Faanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, and J. A. Pople, Gaussian 03, Revision C. 02, Gaussian Inc., Wallingford CT 2004.
G. M. Sheldrick, Acta Crystallogr., A64, 112 (2008).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, 387–392, March, 2011.
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Shestakov, A.S., Bushmarinov, I.S., Sidorenko, O.E. et al. Structure of the product of the interaction of methyl anthranilate with N-(4,6-dimethylpyrimidin-2-yl)cyanamide. Chem Heterocycl Comp 47, 316–320 (2011). https://doi.org/10.1007/s10593-011-0759-3
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DOI: https://doi.org/10.1007/s10593-011-0759-3