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Synthesis, Characterization and Crystal Structure of N-(4-(4-Fluorophenyl)-5-(hydroxymethyl)-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide
Corresponding Author(s) : Jia-Ying Xu
Asian Journal of Chemistry,
Vol. 26 No. 22 (2014): Vol 26 Issue 22
Abstract
N-[4-(4-Fluorophenyl)-5-(hydroxymethyl)-6-isopropylpyrimidin-2-yl]-N-methylmethane sulfonamide (I), an important intermediate to synthesize rosuvastatin, an HMG-CoA reductase inhibitor. It was prepared from methyl 4-(4-fluorophenyl)-6-isopropyl-2-(methylamino)pyrimidine-5-carboxylate (1) via mesylation by mesyl chloride and sodium tert-pentoxide, then reduction by DIBAL/HCl. The product was characterized by NMR and LC-MS. The crystal structure of compound I was investigated using X-ray diffraction and SHELXTL-97 software. The result indicated that compound I crystallized in the monoclinic system, space group C2/C with a = 29.683(6), b = 7.6290 (15), c = 18.215(4) Å, V = 3451.1 (16) Å3; Z 8.
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- M. Vasudevan, J. Ravi, S. Ravisankar and B. Suresh, J. Pharm. Biomed. Anal., 25, 77 (2001); doi:10.1016/S0731-7085(00)00493-3.
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- Q. Jeremy, T. Mark and K. Peter, News Analysis, 2, 769 (2003).
- L. Wenqing, Z. Hongjie and P. Yang, US Patent 20130143908 (2013).
- D. Šterk, Z. Casar, M. Jukic and J. Košmrlj, Tetrahedron, 68, 2155 (2012); doi:10.1016/j.tet.2012.01.013.
- L. Jing-lin and H. Hua-rong, CN Patent 201010245642 (2010).
- H. Zhong-bin, D. Lian-hua and H. Yong, CN Patent 200810146732 (2008).
- L. Kai-Chao, CN Patent 201210069448 (2012).
- F.H. Allen, O. Kennard, D.G. Watson, L. Brammer, A.G. Orpen and R. Taylor, J. Chem. Soc., Perkin Trans. 2, S1 (1987); doi:10.1039/p298700000s1.
- J. Folkman, Sci. Am., 275, 150 (1996); doi:10.1038/scientificamerican0996-150.
- A.C.T. North, D.C. Phillips and F.S. Mathews, Acta Crystallogr. A, 24, 351 (1968); doi:10.1107/S0567739468000707.
- G.M. Sheldrick, Acta Crystallogr. A, 64, 112 (2008); doi:10.1107/S0108767307043930.
References
M. Vasudevan, J. Ravi, S. Ravisankar and B. Suresh, J. Pharm. Biomed. Anal., 25, 77 (2001); doi:10.1016/S0731-7085(00)00493-3.
E. Nicole and R. Yvonne, WO Patent 2004103977 (2004).
C. Zdenko and S. Damjan, WO Patent 2012013325 (2012).
Q. Jeremy, T. Mark and K. Peter, News Analysis, 2, 769 (2003).
L. Wenqing, Z. Hongjie and P. Yang, US Patent 20130143908 (2013).
D. Šterk, Z. Casar, M. Jukic and J. Košmrlj, Tetrahedron, 68, 2155 (2012); doi:10.1016/j.tet.2012.01.013.
L. Jing-lin and H. Hua-rong, CN Patent 201010245642 (2010).
H. Zhong-bin, D. Lian-hua and H. Yong, CN Patent 200810146732 (2008).
L. Kai-Chao, CN Patent 201210069448 (2012).
F.H. Allen, O. Kennard, D.G. Watson, L. Brammer, A.G. Orpen and R. Taylor, J. Chem. Soc., Perkin Trans. 2, S1 (1987); doi:10.1039/p298700000s1.
J. Folkman, Sci. Am., 275, 150 (1996); doi:10.1038/scientificamerican0996-150.
A.C.T. North, D.C. Phillips and F.S. Mathews, Acta Crystallogr. A, 24, 351 (1968); doi:10.1107/S0567739468000707.
G.M. Sheldrick, Acta Crystallogr. A, 64, 112 (2008); doi:10.1107/S0108767307043930.