Titanium(IV) isopropoxide mediated synthesis of pyrimidin-4-ones

Organic Letters

Volumn 12, Issue 10, 2010, Pages 2270-2273

  Ramanjulu, Joshi M ^a   Demartino, Michael P ^a   Lan, Yunfeng ^a   Marquis, Robert ^a  

^a GLAXOSMITHKLINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOMETALLIC COMPOUND; PYRIMIDINONE DERIVATIVE; TITANIUM ISOPROPOXIDE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

CATALYSIS; CRYSTALLOGRAPHY, X-RAY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PYRIMIDINONES; STEREOISOMERISM;

EID: 77952327901     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol100624p     Document Type: Article

References (19)

1. Madaan, V. Drugs Today 2009, 45 (1) 55-62
2. Nugent, R. A.; Schlachter, S. T. PCT Int. Appl. 1995, WO9511235A1.
3. Bagli, J.; Bogri, T.; Palameta, B.; Rakhit, S.; Peseckis, S.; McQuillan, J.; Lee, D. K. H. J. Med. Chem. 1988, 31, 814
4. Belyk, K. M.; Morrison, H. G.; Jones, P.; Summa, V. PCT Int. Appl. 2006, WO2006060712A2.
5. Madhavan, G. R.; Chakrabarti, R.; Vikramadithyan, R. K.; Mamidi, R. N. V. S.; Balaraju, V.; Rajesh, B. M.; Misra, P.; Kumar, S. K. B.; Lohray, B. B.; Lohray, V. B.; Rajagopalan, R. Bioorg. Med. Chem. 2002, 2671
6. Hoornaert, C.; Wick, A. Eur. Pat. Appl. 1994, EP 607077 A1.
7. Reboud-Ravaux, M. J. Soc. Biol. 2001, 195, 143
8. Pinner, A. Chem. Ber. 1889, 22, 1612
9. Salimbeni, A.; Canevotti, R.; Paleari, F.; Poma, D.; Caliari, S.; Fici, F.; Cirillo, R.; Renzetti, A.; Subissi, A.; Belvisi, L.; Bravi, G.; Scolastico, C.; Giachetti, A. J. Med. Chem. 1995, 38, 4806
10. Jezewski, A.; Jurczak, J.; Lidert, Z.; Tice, C. M. J. Heterocycl. Chem. 2001, 38, 645
11. Jeong, J. U.; Chen, X.; Rahman, A.; Yamashita, D.; Luengo, J. I. Org. Lett. 2004, 6, 1013
12. Takahashi, T.; Hirokami, S.; Nagata, M. J. Chem. Soc., Perkin Trans. 1 1998, 2653
13. Grayson, D. H.; Tuite, M. R. J. Chem. Soc., Perkin Trans. 1 1986, 2137
14. Addition of ethanol aids in absorption of microwave irradiation.
15. See Supporting Information for general procedure.
16. 4] generated no detectable/trace amounts of product by LCMS analysis.
17. Han, C.; Lee, J. P.; Lobkovsky, E.; Porco, J. A., Jr. J. Am. Chem. Soc. 2005, 127, 10039
18. It is known that the transesterification of titanium(IV) isopropoxide is known to be kinetically slow: Paquette, L. Handbook of reagents for organic synthesis-Activating agents and protecting groups; John Wiley & Sons: New York, 1999; pp 389 - 394.
19. For synthesis of 3-fluoro-2-hydroxy benzamide, see: patent WO2007062370A2.