One-pot double Suzuki couplings of dichloropyrimidines

Synthesis

Volumn , Issue 16, 2010, Pages 2721-2724

  Anderson, Samantha C ^a   Handy, Scott T ^a  

^a MIDDLE TENNESSEE STATE UNIVERSITY   (United States)

Author keywords

one pot reaction; palladium catalyzed; pyrimidines; regioselectivity; suzuki coupling

Indexed keywords

ALCOHOLIC SOLVENTS; EFFICIENT SYNTHESIS; ONE POT; ONE-POT REACTION; POLAR APROTIC SOLVENT; REACTION SEQUENCES; REGIO-SELECTIVE; SUZUKI COUPLINGS;

AROMATIC COMPOUNDS; PALLADIUM; REGIOSELECTIVITY; SOLVENTS;

SYNTHESIS (CHEMICAL);

2 (2 METHOXYPHENYL) 4 PHENYLPYRIMIDINE; 2 (4 FLUOROPHENYL) 4 PHENYLPYRIMIDINE; 2 (HEPT 1 ENYL) 4 (4 METHOXYPHENYL)PYRIMIDINE; 2 CHLORO 4 PHENYLPYRIMIDINE; 4 (2 METHOXYPHENYL) 2 PHENYLPYRIMIDINE; 4 (4 METHOXYPHENYL) 2 PHENYLPYRIMIDINE; 4 (HEPT 1 ENYL) 2 (4 METHOXYPHENYL)PYRIMIDINE; 4 PHENYL 2 (4 METHOXYPHENYL)PYRIMIDINE; ALCOHOL; DICHLOROPYRIMIDINE DERIVATIVE; IMATINIB; METHANOL; PYRIMIDINE DERIVATIVE; ROSUVASTATIN; SOLVENT; TOLUENE; UNCLASSIFIED DRUG; WATER;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; DRUG STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ONE POT SYNTHESIS; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; SUZUKI REACTION; TEMPERATURE; THIN LAYER CHROMATOGRAPHY;

EID: 77955401725     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0030-1258150     Document Type: Article

References (31)

1. For examples, see: Name Reactions in Heterocyclic Chemistry Li J J. Wiley New York 2005 536
2. Li J J., Gribble G W., Palladium in Heterocyclic Chemistry: A Guide for the Synthetic Chemist Elsevier London 2007 475
3. Varallo S, Handy S T., Synthesis 2009 138
4. Handy S T., Mayi D, Tetrahedron Lett. 2007 46 8108
5. Handy S T., Wilson T, Muth A, J. Org. Chem. 2007 72 48496
6. Zhang Y, Handy S T., Open Org. Chem. J. 2008 58
7. Handy S T., Zhang Y, Synthesis 2006 3883
8. Handy S T., Sabatini J J., Org. Lett. 2006 8 1537
9. For a review of regioselective couplings of heteroaromatic systems, see:, Schroeter S, Stock C, Bach T, Tetrahedron 2005 61 2245
10. Fairlamb I. J. S, Chem. Soc. Rev. 2007 36 1036
11. Handy S T., Zhang Y, Chem. Commun. 2006 299
12. For the earliest report of regioselectivity in a cross-coupling of 2,4-dichloropyrimidine, see:, Solberg J, Undheim K, Acta Chem. Scand. 1989 43 62
13. Garcia Y, Schoenebeck F, Legault C Y., Merlic C A., Houk K N., J. Am. Chem. Soc. 2009 131 6632
14. Rheault T R., Donaldson K H., Cheung M, Tetrahedron Lett. 2009 50 1399
15. Gong B, Hong F, Kohm C, Jenkins S, Tulinsky J, Bhatt R, deVries P, Singer J W., Klein P, Bioorg. Med. Chem. Lett. 2004 14 2303
16. Blackaby W P., Atack J R., Bromidge F, Castro J L., Goodacre S C., Hallett D J., Lewis R T., Marshall G R., Pike A, Smith A J., Street L J., Tattersall D F. D., Wafford K A., Bioorg. Med. Chem. Lett. 2006 16 1175
17. Wang X, Chakrabarti P P., Ognyanov V I., Pettus L H., Tamir R, Tan H, Tang P, Treanor J J. S., Gavva N R., Norman M H., Bioorg. Chem. Lett. 2007 17 6539
18. Parry P R., Wang C, Batsanov A S., Bryce M R., Tarbit B, J. Org. Chem. 2002 67 7541
19. Delia T J., Schomaker J M., Kalinda A S., J. Heterocycl. Chem. 2006 43 127
20. Ceide S C., Montalban A G., Tetrahedron Lett. 2006 47 4415
21. Schomaker J M., Delia T J., J. Org. Chem. 2001 66 7125
22. Colombo M, Giglio M, Peretto I, J. Heterocycl. Chem. 2008 45 1077
23. Liu J, Fitzgerald A E., Mani N S., J. Org. Chem. 2008 73 2951
24. Cocuzza A J., Hobbs F W., Arnold C R., Chidester D R., Yarem J A., Culp S, Firzgerald L, Gilligan P J., Bioorg. Med. Chem. Lett. 1999 9 1057
25. Gong Y, Pauls H W., Synlett 2000 829
26. Mavunkel B, Xu Y, Goyal B, Lim D, Lu Q, Chen Z, Wang D, Higaki J, Chakraborty I, Liclican A, Sideris S, Laney M, Delling U, Catalano R, Higgins L S., Wang H, Wang J, Feng Y, Dugar S, Levy D E., Bioorg. Med. Chem. Lett. 2008 18 2404
27. Geneste H, Sauer D, German Patent DE 102004061593 2006\
28. Chem. Abstr. 2006, 145, 83384
29. Colombo M, Giglio M, Peretto I, J. Heterocycl. Chem. 2008 45 1077
30. Abbiati G, Arcadi A, Canevari V, Rossi E, Tetrahedron Lett. 2007 48 8491
31. Seki M, Kubota H, Matsumoto K, Kinumaki A, Da-te T, Okamura K, J. Org. Chem. 1993 58 6354