Efficient synthesis of 4-aminoquinazoline and thieno[3,2-d]pyrimidin-4- ylamine derivatives by microwave irradiation

Organic Letters

Volumn 6, Issue 25, 2004, Pages 4775-4778

  Yoon, David S ^a   Han, Ying ^a   Stark, Todd M ^a   Haber, James C ^a   Gregg, Brian T ^a   Stankovich, Sara B ^a  

^a ALBANY MOLECULAR RESEARCH INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 AMINOQUINAZOLINE; AMINE; QUINAZOLINE DERIVATIVE; SOLVENT; THIENO[3,2 D]PYRIMIDIN 4 YLAMINE; UNCLASSIFIED DRUG;

ARTICLE; MICROWAVE IRRADIATION; REACTION TIME; SYNTHESIS; TEMPERATURE;

EID: 11444265468     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol047919y     Document Type: Article

References (18)

1. Johne, S. The Alkaloids, Chemistry and Pharmacology; Brossi, A., Ed.; 1986; Vol. 29, pp 99-140.
2. For recent review, see: (a) Fry, D. W.; Kraker, A. J.; McMichael, A.; Ambroso, L. A.; Nelson, J. M.; Leopold, W. R.; Connors, R. W.; Bridges, A. J. Science 1994, 265, 1093-1095. (b) Bridges, A. J. Chem. Rev. 2001, 101, 2541-2572. (c) Tsou, H. R.; Mamuya, N.; Johnson, B. D.; Reich, M. F.; Gruber, B. C.; Ye, F.; Nilakantan, R.; Shen, R.; Discafani, C.; DeBlanc, R.; Davis, R.; Koehn, R. E.; Greenberger, L. M.; Wang, Y. F.; Wissner, A. J. Med. Chem. 2001, 44, 2719-2734. (d) Berger, M.; Albrecht, B.; Berces, A, Ettmayer, P.; Neruda, W.; Woisetschläger, M. J. Med. Chem. 2001, 44, 3031-3038.
3. For recent review, see: (a) Fry, D. W.; Kraker, A. J.; McMichael, A.; Ambroso, L. A.; Nelson, J. M.; Leopold, W. R.; Connors, R. W.; Bridges, A. J. Science 1994, 265, 1093-1095. (b) Bridges, A. J. Chem. Rev. 2001, 101, 2541-2572. (c) Tsou, H. R.; Mamuya, N.; Johnson, B. D.; Reich, M. F.; Gruber, B. C.; Ye, F.; Nilakantan, R.; Shen, R.; Discafani, C.; DeBlanc, R.; Davis, R.; Koehn, R. E.; Greenberger, L. M.; Wang, Y. F.; Wissner, A. J. Med. Chem. 2001, 44, 2719-2734. (d) Berger, M.; Albrecht, B.; Berces, A, Ettmayer, P.; Neruda, W.; Woisetschläger, M. J. Med. Chem. 2001, 44, 3031-3038.
4. For recent review, see: (a) Fry, D. W.; Kraker, A. J.; McMichael, A.; Ambroso, L. A.; Nelson, J. M.; Leopold, W. R.; Connors, R. W.; Bridges, A. J. Science 1994, 265, 1093-1095. (b) Bridges, A. J. Chem. Rev. 2001, 101, 2541-2572. (c) Tsou, H. R.; Mamuya, N.; Johnson, B. D.; Reich, M. F.; Gruber, B. C.; Ye, F.; Nilakantan, R.; Shen, R.; Discafani, C.; DeBlanc, R.; Davis, R.; Koehn, R. E.; Greenberger, L. M.; Wang, Y. F.; Wissner, A. J. Med. Chem. 2001, 44, 2719-2734. (d) Berger, M.; Albrecht, B.; Berces, A, Ettmayer, P.; Neruda, W.; Woisetschläger, M. J. Med. Chem. 2001, 44, 3031-3038.
5. For recent review, see: (a) Fry, D. W.; Kraker, A. J.; McMichael, A.; Ambroso, L. A.; Nelson, J. M.; Leopold, W. R.; Connors, R. W.; Bridges, A. J. Science 1994, 265, 1093-1095. (b) Bridges, A. J. Chem. Rev. 2001, 101, 2541-2572. (c) Tsou, H. R.; Mamuya, N.; Johnson, B. D.; Reich, M. F.; Gruber, B. C.; Ye, F.; Nilakantan, R.; Shen, R.; Discafani, C.; DeBlanc, R.; Davis, R.; Koehn, R. E.; Greenberger, L. M.; Wang, Y. F.; Wissner, A. J. Med. Chem. 2001, 44, 2719-2734. (d) Berger, M.; Albrecht, B.; Berces, A, Ettmayer, P.; Neruda, W.; Woisetschläger, M. J. Med. Chem. 2001, 44, 3031-3038.
6. (a) Reference 2c.
7. (b) Rocco, S. A.; Barbarini, J. E.; Rittner, R. Synthesis 2004, 3, 429-435 and references cited therein.
8. Gedye, R.; Smith, F.; Westaway, K.; Ali, H.; Baldisera, L. Tetrahedron Lett. 1986, 27, 279-282.
9. For recent reviews on microwave-assisted chemistry, see: (a) Perio, B.; Dozias, M.; Hamelin, J. Org. Process Res. Dev. 1998, 2, 428-430. (b) Cleophax, J.; Liagre, M.; Loupy, A.; Petit, A. Org. Process Res. Dev. 2000, 4, 498-504. (c) Perreux, L.; Loupy, A. Tetrahedron 2001, 57, 9199-9223. (d) Lidstrom, P.; Tierney, J.; Wathey, B.; Westman, J. Tetrahedron 2001, 57, 9225-9283. (e) Lew, A.; Krutzik, P. O.; Hart, M. E.; Chamberlin, A. R. J. Comb. Chem. 2002, 4, 95-105. (f) Santagada, V.; Perissutti, E.; Caliendo, G. Curr. Med. Chem. 2002, 9, 1251-1283. (g) Mavandadi, F.; Lidstrom, P. Curr. Top. Med. Chem. 2004, 4, 773-792.
10. For recent reviews on microwave-assisted chemistry, see: (a) Perio, B.; Dozias, M.; Hamelin, J. Org. Process Res. Dev. 1998, 2, 428-430. (b) Cleophax, J.; Liagre, M.; Loupy, A.; Petit, A. Org. Process Res. Dev. 2000, 4, 498-504. (c) Perreux, L.; Loupy, A. Tetrahedron 2001, 57, 9199-9223. (d) Lidstrom, P.; Tierney, J.; Wathey, B.; Westman, J. Tetrahedron 2001, 57, 9225-9283. (e) Lew, A.; Krutzik, P. O.; Hart, M. E.; Chamberlin, A. R. J. Comb. Chem. 2002, 4, 95-105. (f) Santagada, V.; Perissutti, E.; Caliendo, G. Curr. Med. Chem. 2002, 9, 1251-1283. (g) Mavandadi, F.; Lidstrom, P. Curr. Top. Med. Chem. 2004, 4, 773-792.
11. For recent reviews on microwave-assisted chemistry, see: (a) Perio, B.; Dozias, M.; Hamelin, J. Org. Process Res. Dev. 1998, 2, 428-430. (b) Cleophax, J.; Liagre, M.; Loupy, A.; Petit, A. Org. Process Res. Dev. 2000, 4, 498-504. (c) Perreux, L.; Loupy, A. Tetrahedron 2001, 57, 9199-9223. (d) Lidstrom, P.; Tierney, J.; Wathey, B.; Westman, J. Tetrahedron 2001, 57, 9225-9283. (e) Lew, A.; Krutzik, P. O.; Hart, M. E.; Chamberlin, A. R. J. Comb. Chem. 2002, 4, 95-105. (f) Santagada, V.; Perissutti, E.; Caliendo, G. Curr. Med. Chem. 2002, 9, 1251-1283. (g) Mavandadi, F.; Lidstrom, P. Curr. Top. Med. Chem. 2004, 4, 773-792.
12. For recent reviews on microwave-assisted chemistry, see: (a) Perio, B.; Dozias, M.; Hamelin, J. Org. Process Res. Dev. 1998, 2, 428-430. (b) Cleophax, J.; Liagre, M.; Loupy, A.; Petit, A. Org. Process Res. Dev. 2000, 4, 498-504. (c) Perreux, L.; Loupy, A. Tetrahedron 2001, 57, 9199-9223. (d) Lidstrom, P.; Tierney, J.; Wathey, B.; Westman, J. Tetrahedron 2001, 57, 9225-9283. (e) Lew, A.; Krutzik, P. O.; Hart, M. E.; Chamberlin, A. R. J. Comb. Chem. 2002, 4, 95-105. (f) Santagada, V.; Perissutti, E.; Caliendo, G. Curr. Med. Chem. 2002, 9, 1251-1283. (g) Mavandadi, F.; Lidstrom, P. Curr. Top. Med. Chem. 2004, 4, 773-792.
13. For recent reviews on microwave-assisted chemistry, see: (a) Perio, B.; Dozias, M.; Hamelin, J. Org. Process Res. Dev. 1998, 2, 428-430. (b) Cleophax, J.; Liagre, M.; Loupy, A.; Petit, A. Org. Process Res. Dev. 2000, 4, 498-504. (c) Perreux, L.; Loupy, A. Tetrahedron 2001, 57, 9199-9223. (d) Lidstrom, P.; Tierney, J.; Wathey, B.; Westman, J. Tetrahedron 2001, 57, 9225-9283. (e) Lew, A.; Krutzik, P. O.; Hart, M. E.; Chamberlin, A. R. J. Comb. Chem. 2002, 4, 95-105. (f) Santagada, V.; Perissutti, E.; Caliendo, G. Curr. Med. Chem. 2002, 9, 1251-1283. (g) Mavandadi, F.; Lidstrom, P. Curr. Top. Med. Chem. 2004, 4, 773-792.
14. For recent reviews on microwave-assisted chemistry, see: (a) Perio, B.; Dozias, M.; Hamelin, J. Org. Process Res. Dev. 1998, 2, 428-430. (b) Cleophax, J.; Liagre, M.; Loupy, A.; Petit, A. Org. Process Res. Dev. 2000, 4, 498-504. (c) Perreux, L.; Loupy, A. Tetrahedron 2001, 57, 9199-9223. (d) Lidstrom, P.; Tierney, J.; Wathey, B.; Westman, J. Tetrahedron 2001, 57, 9225-9283. (e) Lew, A.; Krutzik, P. O.; Hart, M. E.; Chamberlin, A. R. J. Comb. Chem. 2002, 4, 95-105. (f) Santagada, V.; Perissutti, E.; Caliendo, G. Curr. Med. Chem. 2002, 9, 1251-1283. (g) Mavandadi, F.; Lidstrom, P. Curr. Top. Med. Chem. 2004, 4, 773-792.
15. For recent reviews on microwave-assisted chemistry, see: (a) Perio, B.; Dozias, M.; Hamelin, J. Org. Process Res. Dev. 1998, 2, 428-430. (b) Cleophax, J.; Liagre, M.; Loupy, A.; Petit, A. Org. Process Res. Dev. 2000, 4, 498-504. (c) Perreux, L.; Loupy, A. Tetrahedron 2001, 57, 9199-9223. (d) Lidstrom, P.; Tierney, J.; Wathey, B.; Westman, J. Tetrahedron 2001, 57, 9225-9283. (e) Lew, A.; Krutzik, P. O.; Hart, M. E.; Chamberlin, A. R. J. Comb. Chem. 2002, 4, 95-105. (f) Santagada, V.; Perissutti, E.; Caliendo, G. Curr. Med. Chem. 2002, 9, 1251-1283. (g) Mavandadi, F.; Lidstrom, P. Curr. Top. Med. Chem. 2004, 4, 773-792.
16. Cai, L.; Han, Y.; Ren, S. M.; Huang, L. F. Tetrahedron 2000, 56, 8253-8262.
17. Typical Experimental Procedure. To a 5 mL microwave reaction vial equipped with a magnetic stir bar were added N′-(2-cyano-3-fluorophenyl)- N,N-dimethylformamidine 1a (100 mg, 0.52 mmol) and 2-chlorobenzylamine 2a (90 mg, 0.62 mmol), followed by a 30% solution of glacial acetic acid in acetonitrile (2 mL). The mixture was capped and irradiated in the microwave for 10 min at 160°C, cooled to ambient temperature, and purified in parallel using the following procedure: the contents of the vial were emptied onto a fritted solid sample cartridge (70 mL) loaded with Hydromatrix (12 g) pretreated with a solution of saturated sodium bicarbonate (20 mL). The solution was eluted directly onto a second solid sample cartridge (70 mL) containing a layer of dry Hydromatrix (4 g) followed by a layer of silica gel (10 g). The cartridges were eluted with ethyl acetate (5 x 20 mL), and the solvent was removed under nitrogen and dried in vacuo to yield 3a (141 mg, 0.49 mmol, 93%) as a white solid.
18. Munchhof, M. J.; Beebe, J. S.; Casavant, J. M.; Beth A. Cooper, Doty, J. L.; R. Higdon, R. C.; Hillerman, S. M.; Soderstrom, C. I.; Knauth, E. A.; Marx, M. A.; Rossi, A.; Sobolov S. B.; Sun, J. Bioorg. Med. Chem. Lett. 2004, 14, 21-24.