A general regioselective synthesis of 2,4-diarylpyrimidines from 2-thiouracil through two orthogonal cross-coupling reactions

Synlett

Volumn 23, Issue 9, 2012, Pages 1305-1308

  Čerňová, Miroslava ^a,b   Pohl, Radek ^b   Klepetářová, Blanka ^b   Hocek, Michal ^a,b  

^a CHARLES UNIVERSITY   (Czech Republic)

^b INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

Author keywords

arylation; cross coupling; microwave; palladium; pyrimidines; uracil

Indexed keywords

2 (METHYLSULFANYL) 4 (3,4,5 TRIMETHOXYPHENYL)PYRIMIDINE; 2 (METHYLSULFANYL) 4 ARYLPYRIMIDINE DERIVATIVE; 2 (METHYLSULFANYL) 4 PHENYLPYRIMIDINE; 2 (METHYLSULFANYL)PYRIMIDIN 4(3H) ONE; 2 METHYLSUFANYL 4 OXO (3H) PYRIMIDINE; 2,4 DIARYLPYRIMIDINE DERIVATIVE; 3 FLUORO 4 METHOXY PHENYLBORONIC ACID DERIVATIVE; 3,4 METHYLENEDIOXY PHENYLBORONIC ACID DERIVATIVE; 3,4,5 TRIMETHOXY PHENYLBORONIC ACID DERIVATIVE; 4 ARYL 2 METHYLSULFANYLPYRIMIDINE DERIVATIVE; 4 METHOXY PHENYLBORONIC ACID DERIVATIVE; 4 PHENYL 2 4 TOLYLPYRIMIDINE; 4 PHENYL 2 PARA TOLYLPYRIMIDINE; BENZENEBORONIC ACID; PHOSPHONIUM DERIVATIVE; PYRIDONE DERIVATIVE; PYRIMIDINE DERIVATIVE; THIOURACIL; UNCLASSIFIED DRUG;

ARTICLE; ARYLATION; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; CRYSTAL STRUCTURE; CYTOSTASIS; METHYLATION; MICROWAVE IRRADIATION; REGIOSELECTIVE SYNTHESIS; SUBSTITUTION REACTION; SUZUKI REACTION; SYNTHESIS; TAUTOMERIZATION;

EID: 84860573519     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0031-1290826     Document Type: Article

References (25)

1. Yaziji V, Rodrguez D, Gutirrez-de-Tern G, Coelho A, Caamano O, Garca-Mera X, Brea J, Loza MI, Cadavid MI, Sotelo E. J. Med. Chem.: 2011; 54 457
2. Large JM, Torr JE, Raynaud FI, Clarke PA, Hayes A, Stefano F, Urban F, Shuttleworth SJ, Saghir N, Sheldrake P, Workman P, McDonald E. Bioorg. Med. Chem.: 2011; 19 836
3. Guay D, Beaulieu Ch, Belley M, Crane SN, DeLuca J, Gareau Y, Hamel M, Henault M, Hyjazie H, Kargman S, Chan CC, Xu L, Gordon R, Li L, Mamane Y, Morin N, Mancini J, Thrien M, Tranmer G, Truong VL, Wang Z, Black WC. Bioorg. Med. Chem. Lett.: 2011; 21 2832
4. Erdmann F, Weiwad M, Kilka S, Karanik M, Patzel M, Baumgrass R, Liebscher J, Fischer G. J. Biol. Chem.: 2010; 285 1888
5. Veldhoven JP. D, Chang LC. W, Kunzel JK. F. D, Mulder-Krieger T, Struensee-Link R, Beukers MW, Brussee J, Ijzerman AP. Bioorg. Med. Chem.: 2008; 16 2741
6. Yan S, Tang Y, Yu F, Lin J. Helv. Chim. Acta: 2011; 94 487
7. Lin M, Chen Q.-Z, Zhu Y, Chen X.-L, Cai J.-J, Pan Y.-M, Zhan Z.-P. Synlett: 2011; 1179
8. Bagley MC, Lin Z, Pope SJ. A. Tetrahedron Lett.: 2009; 50 6818
9. Anderson SC, Handy ST. Synthesis: 2010; 2721
10. Parry PR, Wang C, Batsanov AS, Bryce MR, Tarbit B. J. Org. Chem.: 2002; 67 7541
11. Schomaker JM, Delia TJ. J. Org. Chem.: 2001; 66 7125
12. Mansour TS, Bardhan S, Wan Z.-K. Synlett: 2010; 1143
13. Original paper: Kang F.-A, Sui Z, Murray WV. J. Am. Chem. Soc.: 2008; 130 11300
14. Prokopcov H, Kappe CO. Angew. Chem. Int. Ed.: 2009; 48 2276
15. Original paper: Liebeskind LS, Srogl J. Org. Lett.: 2002; 4 979
16. Kusturin C, Liebeskind LS, Rahman H, Sample K, Schweitzer B, Srogl J, Neumann WL. Org. Lett.: 2003; 5 4349
17. Singh BK, Mehta VP, Parmar VS, Van der Eycken E. Org. Biomol. Chem.: 2007; 5 2962
18. Bibby MC. Drugs Future: 2002; 27 475
19. Tron GC, Piralli T, Sorba G, Pagliai F, Busacca S, Genazzani AA. J. Med. Chem.: 2006; 49 3033
20. Bonezzi K, Taraboletti G, Borsotti P, Bellina F, Rossi R, Giavazzi R. J. Med. Chem.: 2009; 52 7906
21. Theeramungkong S, Caldarelli A, Mussarotti A, Aprile S, Caprioglio D, Zaninetti R, Teruggi A, Piralli T, Grosa G, Tron GC, Genazzi AA. J. Med. Chem.: 2011; 54 4977
22. Schöter S, Stock C, Bach T. Tetrahedron: 2005; 61 2245
23. Fairlamb IJ. S. Chem. Soc. Rev.: 2007; 36 1036
24. Examples: Hocek M, Pohl R. Synthesis: 2004; 2869
25. See also: Kubelka T, Slavtnsk L, Klepetov B, Hocek M. Eur. J. Org. Chem.: 2010; 2666