RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000083.xml
Synlett 2014; 25(07): 935-938
DOI: 10.1055/s-0033-1340860
DOI: 10.1055/s-0033-1340860
letter
Microwave-Assisted Synthesis of 4-Substituted 2-Methylthiopyrimidines
Weitere Informationen
Publikationsverlauf
Received: 06. Januar 2014
Accepted after revision: 04. Februar 2014
Publikationsdatum:
24. März 2014 (online)
![](https://www.thieme-connect.de/media/synlett/201407/lookinside/thumbnails/10.1055-s-0033-1340860-1.jpg)
Abstract
Typically, SNAr reactions at 4-chloro-2-methylthiopyrimidine are carried out employing DMF and sodium hydride under inert gas as well as prolonged reaction times. Herein, we describe a mild and rapid microwave-assisted synthesis to achieve 4-substituted 2-methylthiopyrimidnes from the corresponding chlorine precursor. Moderate to excellent yields were obtained in a green chemistry fashion requiring only few minutes of reaction time.
Key words
green chemistry - pyrimidine - combinatorial chemistry - medicinal chemistry - nucleophilic aromatic substitutionSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
- Supporting Information
-
References
- 1 Goldstein DM, Gong L, Michoud C, Palmer WS, Sidduri A. US Patent WO 2008028860 (A1), 2008
- 2 Goulet Joung L, Holmes MA, Hunt JA, Mills SG, Parsons WH, Sinclair PJ, Zaller D. US Patent WO 0100207 (A1), 2001
- 3 Beresis RT, Goulet JL, Hermes JD, Holmes MA, Hong XJ, Hunt JA, Kovacs E, Mills SG, Park Y.-W, Ruzek RD, Salowe SP, Sinclair PJ, Sonatore LM, Wong F, Woods A, Wu L, Zaller DM. Bioorg. Med. Chem. Lett. 2009; 19: 5440
- 4 Balitza AE, Bilodeau MT, Coll KE, Hartman GD, Manley PJ, McFall RC, Rickert KW, Rodman LD, Thomas KA. Bioorg. Med. Chem. Lett. 2003; 13: 1673
- 5 Kim M.-H, Lee J, Jung K, Kim M, Park Y.-J, Ahn H, Kwon Y, Hah J.-M. Bioorg. Med. Chem. 2013; 21: 2271
- 6 Borowski T, Mokrosz MJ, Krol M, Broclawik E, Baranowski TC, Strekowski L. J. Med. Chem. 2000; 43: 1901
- 7 Ikeda M, Maruyama K, Okabe S, Nobuhara Y, Yamada T. Chem. Pharm. Bull. 1997; 45: 549
- 8 Lukasik PM, Elabar S, Lam F, Shao H, Liu X, Abbas AY, Wang S, Lam F, Wang S. Eur. J. Med. Chem. 2012; 57: 311
- 9 Chung JY, Hah J.-M, Kim H, Lee J, Oh C.-H, Sim T, Yoo KH, Yu H. Bioorg. Med. Chem. Lett. 2010; 20: 1573
-
11 Vera-Luque P, Alajarin R, Alvarez-Builla J, Vaquero JJ. Org. Lett. 2006; 8: 415
- 12 Kappe CO. Angew. Chem. Int. Ed. 2004; 43: 6250
- 13 de la Hoz ADiaz-Ortiz A. Moreno A. Chem. Soc. Rev. 2005; 164
- 14 Vorobiov AN, Gaponik PN, Petrov PT, Ivashkevich OA. Synthesis 2006; 1307
- 15 Su W.-K, Hong Z, Shan W.-G, Zhang X.-X. Eur. J. Org. Chem. 2006; 2723
- 16 Ouali A, Taillefer M, Xia N. Angew. Chem. Int. Ed. 2007; 46: 934
- 17 Wright JB. Chem. Rev. 1951; 48: 397
- 18 Larinaa LI, Milatab V. Magn. Reson. Chem. 2009; 47: 142
- 19 Jouvin K, Coste A, Bayle A, Legrand F, Karthikeyan G, Tadiparthi K, Evano G. Organometallics 2012; 31: 7933
- 20 Bentin T, Hamzavi R, Salomonsson J, Roy H, Ibba M, Nielsen PE. J. Biol. Chem. 2004; 279: 19839
- 21 Barlin GB, Batterham TF. J. Chem. Soc. B 1967; 516
- 22 Hurst DT, Johnson M. Heterocycles 1985; 23: 611
- 23 He H, Jin C, Fu L, Liang Y.-J. Eur. J. Med. Chem. 2011; 46: 429
- 24 List B, Castello C. Synlett 2001; 1687