Solvent-free or low-solvent large-scale preparation of chloropyrimidine and analogues

Journal of Organic Chemistry

Volumn 76, Issue 10, 2011, Pages 4149-4153

  Sun, Zhihua ^a,b   Wang, Han ^a   Wen, Kun ^a   Li, Ya ^a   Fan, Erkang ^c  

^a SHANGHAI UNIVERSITY OF ENGINEERING SCIENCE   (China)

^b SHANGHAI INSTITUTE OF MATERIA MEDICA   (China)

^c UNIVERSITY OF WASHINGTON SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

LARGE SCALE PREPARATION; SOLVENT FREE; SYNTHETIC INTERMEDIATES;

SOLVENTS;

2 AMINO 4 CHLOROPYRIMIDINE; 2,4 DICHLORO 5 FLUOROPYRIMIDINE; 2,4 DICHLORO 5 METHOXYPYRIMIDINE; 2,4 DICHLOROPYRIDO[2,3 D]PYRIMIDINE; 2,4 DICHLOROPYRIDO[3,2 D]PYRIMIDINE; 2,4 DICHLOROQUINAZOLINE; 2,6 DICHLORO 9H PURINE; 4 CHLOROPYRIDO[2,3 D]PYRIMIDINE; 6 BROMO 2,4 DICHLOROPYRIDO[2,3 D]PYRIMIDINE; 6 BROMO 4 CHLOROPYRIDO[2,3 D]PYRIMIDINE; AROMATIC NITRO COMPOUND; CHLOROPYRIMIDINE; PYRIMIDINE DERIVATIVE; PYRIMIDINOL; SOLVENT; UNCLASSIFIED DRUG; URACIL;

ARTICLE; BIOTRANSFORMATION; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHLORINATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROXYLATION; NUCLEOPHILICITY; REACTION TIME; STRUCTURE ANALYSIS; SUBSTITUTION REACTION; SYNTHESIS;

GREEN CHEMISTRY TECHNOLOGY; PYRIMIDINES; SOLVENTS;

EID: 79956151545     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo2003715     Document Type: Article

References (34)

1. Gabriel, S. Chem. Ber. 1905, 38, 1690
2. Whittaker, N.; Jones, T. S. G. J. Chem. Soc. 1951, 1565
3. Hunds, A. Chlorination process for the preparation of chloropyrimidines from hydroxypyrimidines or their tautomeric keto forms. GB 2287466, 1995, CAN 124:176135.
4. Leng, R. B.; Ringer, J. W.; Maurer, J. L. Chloropyrimidine Process. US 6066734, 1999, CAN 131:60319.
5. Sugimoto, O.; Mori, M.; Moriya, K.; Tanji, K. I. Helv. Chim. Act. 2001, 84 (5) 1112
6. Zeng, Q.; Huang, B.; Danielsen, K.; Shukla, R.; Nagy, T. Org. Proc. Res. Dev 2004, 8 (6) 962
7. Elion, G. B.; Hitchings, G. H. J. Am. Chem. Soc. 1956, 78 (14) 3508-3510
8. Cherney, R. J. C.; P.; Duncia; J. V.; Gardner; D. S.; Santella, J. B. Preparation of cyclohexyl-substituted lactams as cytokine receptor modulating agents. WO 2004071460, 2004, CAN 141:225304.
9. Robins, R. K.; Hitchings, G. H. J. Am. Chem. Soc. 1955, 77 (8) 2256-2260
10. Block, M. H.; Han, Y.; Josey, J. A.; Lee, J. W.; Scott, D.; Wang, B.; Wang, H.; Wang, T.; Yu, D. Preparation of pyrazole derivatives as inhibitors of receptor tyrosine kinases. WO 2005049033, 2005, CAN 143:7708.
11. Malagu, K.; Duggan, H.; Menear, K.; Hummersone, M.; Gomez, S.; Bailey, C.; Edwards, P.; Drzewiecki, J.; Leroux, F.; Quesada, M. J.; Hermann, G.; Maine, S.; Molyneaux, C.-A.; Le Gall, A.; Pullen, J.; Hickson, I.; Smith, L.; Maguire, S.; Martin, N.; Smith, G.; Pass, M. Bioorg. Med. Chem. Lett. 2009, 19 (20) 5950-5953
12. McLean, A. C.; Spring, F. S. J. Chem. Soc. 1949, 2582-2585
13. Mitchell, I. S.; Spencer, K. L.; Stengel, P.; Han, Y.; Kallan, N. C.; Munson, M.; Vigers, G. P. A.; Blake, J.; Piscopio, A.; Josey, J.; Miller, S.; Xiao, D.; Xu, R.; Rao, C.; Wang, B.; Bernacki, A. L. AKT protein kinase inhibitors for use in treatment of hyperproliferative diseases. WO 2005051304, 2005, CAN 143:40007.
14. Chesterfield, J. H.; McOmie, J. F. W.; Tute, M. S. J. Chem. Soc. 1960, 4590
15. Wang, H. Method for preparing 2,4-dichloro-5-methoxypyrimidine. CN 101486684, 2009, CAN 151:245682.
16. English, J. P. 2-Amino-4-chloropyrimidine. US 2224811, 1940, CAN 35:13465.
17. Duschinsky, R. 2-Chloro-4-amino-5-fluoropyrimidine. US 3185690, 1965, CAN 63:80705.
18. Butters, M.; Ebbs, J.; Green, S. P.; MacRae, J.; Morland, M. C.; Murtiashaw, C. W.; Pettman, A. J. Org. Process Res. Dev. 2001, 5 (1) 28
19. Saidova, F. M.; Gorbunova, G. P. USSR Fiz.-khim. Issled. Sintetich. i Prirod. Soedin., Samarkand 1980, 68-74
20. Prashad, M.; Har, D.; Hu, B.; Kim, H.-Y.; Girgis, M. J.; Chaudhary, A.; Repic, O.; Blacklock, T. J.; Marterer, W. Org. Process Res. Dev. 2004, 8 (3) 330
21. Whitman, D.; Cox, C.; Breslin, M.; Brashear, K.; Schreier, J.; Bogusky, M.; Bednar, R.; Lemaire, W.; Bruno, J.; Hartman, G.; Reiss, D.; Harrell, C. M.; Kraus, R.; Li, Y.; Garson, S.; Doran, S.; Prueksaritanont, T.; Li, C.; Winrow, C.; Koblan, K.; Renger, J.; Coleman, P. ChemMedChem 2009, 4 (7) 1069
22. Tikad, A.; Routier, S.; Akssira, M.; Leger, J.-M.; Jarry, C.; Guillaumet, G. Synlett 2006, 2006 (12) 1938-1942
23. Soloducho, J. Arch. Pharm. 1990, 323 (8) 513-515
24. Chen, G.; Cushing, T. D.; Fisher, B.; He, X.; Li, K.; Li, Z.; McGee, L. R.; Pattaropong, V.; Faulder, P.; Seganish, J. L.; Shin, Y. Alkynyl alcohols as kinase inhibitors and their preparation, pharmaceutical compositions and use in the treatment of inflammation and inflammatory disorders. WO 2009158011, 2009, CAN 152:119631.
25. Bhasin, K. K.; Arora, E.; Kaur, K.; Kang, S. K.; Gobel, M.; Klapoetke, T. M.; Mehta, S. K. Tetrahedron 2009, 65 (1) 247-252
26. Baasner, B.; Klauke, E. J. Fluorine Chem. 1989, 45 (3) 417-430
27. Xie, Y. X.; Pi, S. F.; Wang, J.; Yin, L.; Li, J. H. J. Org. Chem. 2006, 71 (21) 8324-8327
28. Narendar, P.; Gangadasu, B.; Ramesh, C.; Raju, B. C.; Rao, V. J. Synth. Commun. 2004, 34 (6) 1097-1103
29. Coteron, J. M.; Catterick, D.; Castro, J.; Chaparro, M. J.; Diaz, B.; Fernandez, E.; Ferrer, S.; Gamo, F. J.; Gordo, M.; Gut, J.; de las Heras, L.; Legac, J.; Marco, M.; Miguel, J.; Munoz, V.; Porras, E.; de la Rosa, J. C.; Ruiz, J. R.; Sandoval, E.; Ventosa, P.; Rosenthal, P. J.; Fiandor, J. M. J. Med. Chem. 2010, 53 (16) 6129-6152
30. Budesinsky, Z. Cesko-Slov. Farm. 1961, 10, 241
31. Minakawa, N.; Kojima, N.; Hikishima, S.; Sasaki, T.; Kiyosue, A.; Atsumi, N.; Ueno, Y.; Matsuda, A. J. Am. Chem. Soc. 2003, 125 (33) 9970-9982
32. http://riodb01.ibase.aist.go.jp/sdbs/cgi-bin/cre-frame-disp.cgi?sdbsno= 23375.
33. Verbeeck, S.; Herrebout, W. A.; Gulevskaya, A. V.; van der Veken, B. J.; Maes, B. U. W. J. Org. Chem. 2010, 75 (15) 5126-5133
34. Pomel, V.; Gaillard, P.; Desforges, G.; Quattropani, A.; Montagne, C. Preparation of 4-morpholino-pyrido[3,2- d ]pyrimidine compounds as PI3K inhibitors for therapeutic applications. WO 2010037765, 2010, CAN 152:454130.