Browse > Article
http://dx.doi.org/10.12925/jkocs.2008.25.3.4

Synthesis of N,N-Diaryl-(pyridin-3-yl)pyrimidin-2-amine Derivatives and Their Photochemical Properties  

El-Deeb, Ibrahim Mustafa (Department of Biomolecular Science, University of Science and Technology)
Lee, So-Ha (Life Sciences Research Division, Korea Institute of Science and Technology)
Publication Information
Journal of the Korean Applied Science and Technology / v.25, no.3, 2008 , pp. 291-298 More about this Journal
Abstract
Although the pyrimidine derivatives were obtained in low yields ranging from 8% to 20%, we reported the successful preparation of N,N-diaryl-pyrimidin-2-amine derivatives starting from the corresponding 2-aminopyrimidines (1a-1c), by direct palladium-catalyzed arylation using different arylbromides. The reasons of low yields are thought to be the electronic and steric effects by the neighboring aromatic systems. The absorption spectra and photoluminescent spectra of compounds (3a 3g and 4a-4c) were measured using dichloromethane on the concentration of 25 mM by UV vis spectroscopy and luminescent spectroscopy. Pyrimidine derivatives 4a, 4b, and 4c showed moderate emission maxima at 474 nm, 481 nm, and 367 nm, respectively, while other compounds showed very weak photoluminescence or no photoluminescence at all.
Keywords
Palladium catalyst; N,N-diarylation; 2-aminopyrimidine; phosphine ligand;
Citations & Related Records
연도 인용수 순위
  • Reference
1 H. B. Goodbrand and N. X. Hu, Ligand-accelerated catalysis of the Ullmann condensation: application to hole conducting triarylamines. J. Org. Chem., 64, 670 (1999)   DOI   ScienceOn
2 X. Huang, K. W. Anderson, D. Zim, L. Jiang, A. Klapars, and S. L. Buchwald, Expanding Pd-catalyzed C-N bond-forming processes: The first amidation of aryl sulfonates, aqueous amination, and complementarity with Cu-catalyzed reactions. J. Am. Chem. Soc., 125, 6653 (2003)   DOI   ScienceOn
3 D. S. Surry and S. L. Buchwald, Selective palladium-catalyzed arylation of ammonia: synthesis of anilines as well as symmetrical and unsymmetrical di- and triarylamines. J. Am. Chem. Soc., 129, 10354 (2007)   DOI   ScienceOn
4 F. N. Ngassa, K. A. DeKorver, T. S. Melistas, E. A. Yeh, and M. K. Lakshman, Pd-Xantphos-catalyzed direct arylation of nucleosides. Org. Lett., 8, 4613 (2006)   DOI   ScienceOn
5 W. S. Hwang and W. C. Shakespeare, An efficient synthesis of nilotinib (AMN107). Synthesis, 14, 2121 (2007)
6 Y. C. Ku, Y. S. Yen, T. H. Huang, C. H. Chen, J. T. Lin, and C. T. Tsai, Organic electroluminescent bis(diarylamino) dibenzofuran derivatives. J. Chinese Chem. Soc., 53, 1317 (2006)   DOI
7 A. H. Ismail, One pot synthesis of 1-(s-triazolo[4,3-c]pyrimidin-3-yl)substitut ed polyols. Synth. Commun., 32, 1791 (2002)   DOI   ScienceOn
8 K. W. Anderson, R. E. Tundel, T. Ikawa, R. A. Altman, and S. L. Buchwald, Monodentate phosphines provide highly active catalysts for Pd-catalyzed C-N bond-forming reactions of heteroaromatic halides/amines and (H)N-heterocycles. Angew. Chem. Int. Ed., 45, 6523 (2006)   DOI   ScienceOn
9 A. Salcedo, L. Neuville, C. Rondot, P. Retailleau, and J. Zhu, Palladium-catalyzed domino intramolecular N-arylation/intermolecular C-C bond formation for the synthesis of functionalized benzodiazepinediones. Org. Lett., 10, 857 (2008)   DOI   ScienceOn
10 R. A. ltman, B. P. Fors, and S. L. Buchwald, Pd-catalyzed amination reactions of aryl halides using bulky biarylmonophosphine ligands. Nat. Protoc., 2, 2881 (2007)   DOI   ScienceOn
11 J. P. Wolfe, S. Wagaw, and S. L. Buchwald, An improved catalyst system for aromatic carbon-nitrogen bond formation: The possible involvement of bis(phosphine)palladium complexes as key intermediates. J. Am. Chem. Soc., 118, 7215 (1996)   DOI   ScienceOn
12 Y. Harrak, M. Romero, P. Constans, and M. D. Pujol, Preparation of diarylamines and arylhydrazines using palladium catalysts. Lett. Org. Chem., 3, 29 (2006)   DOI
13 I. M. El-Deeb, J. C. Ryu, and S. H. Lee, Synthesis of new N-arylpyrimidin-2-amine derivatives using a palladium catalyst. Molecules, 13, 818 (2008)   DOI   ScienceOn
14 X. Wang, D. V. Gribkov, and D. Sames, Phosphine-free palladium-catalyzed C-H Bond arylation of free (N-H)-indoles and pyrroles. J. Org. Chem., 72, 1476 (2007)   DOI   ScienceOn
15 Y. Fang, R. Karisch and M. Lautens, Efficient syntheses of KDR kinase inhibitors using a Pd-catalyzed tandem C-N/Suzuki coupling as the key step. J. Org. Chem., 72, 1341(2007)   DOI   ScienceOn
16 M. D. Charles, P. Schultz, and S. L. Buchwald, Efficient Pd-catalyzed amination of heteroaryl halides. Org. Lett., 7, 3965 (2005)   DOI   ScienceOn