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A Facile Synthesis of 4,6-Dimethoxy-2-methylsulfonylpyrimidine
Corresponding Author(s) : Defeng Xu
Asian Journal of Chemistry,
Vol. 26 No. 1 (2014): Vol 26 Issue 1
Abstract
A facile and efficient synthesis of 4,6-dimethoxy-2-methylthiopyrimidine can be achieved by nucleophilic substitution of 2-chloro-4,6-dimethoxypyrimidine with sodium methyl mercaptide for a 95.6 % yield. 4,6-Dimethoxy-2-methylsulfonylpyrimidine can be produced via oxidation using hydrogen peroxide in the presence of sodium tungstate dihydrate in a 95 % yield.
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- S.J. Koo, S.C. Ahn, J.S. Lim, S.H. Chae, J.S. Kim, J.H. Lee and J.H. Cho, Pestic. Sci., 51, 109 (1997); doi:10.1002/(SICI)1096-9063(199710)51:2<109::AID-PS585>3.0.CO;2-7.
- 2 K.T. Kim, B.B. Lee, G.H. Joe, et. al., Process for preparing 2, 6-di(4,6-dimethoxy pyrimidin-2-yl) oxybenzoic acid oxime ester derivatives as herbicides, Can. Pat. Appl., 2194080, 1997.
- B. Kanrar and A. Bhattacharyya, J. Environ. Sci. Health B, 44, 788 (2009); doi:10.1080/03601230903238343.
- Y. Nezu, M. Miyazaki, K. Sugiyama, N. Wada, I. Kajiwara and T. Miyazawa, Pestic. Sci., 47, 115 (1996); doi:10.1002/(SICI)1096-9063(199606)47:2<115::AID-PS397>3.0.CO;2-R.
- C.U. Hur, J.H. Cho, S.M. Hong, H.W. Kim, Y.H. Lim, J.S. Rim, J.S. Kim and S.H. Chae, Pyrimidine Derivatives, Process for their Preparation and their Use as Herbicides, EP 658549 A1 (1995).
- C. Luthy, H. Zondler, T. Rapold, G. Seifert, B. Urwyler, T. Heinis, H.C. Steinracken and J. Allen, Pest Manag. Sci., 57, 205 (2001); doi:10.1002/ps.304.
- Z.G. Tian, A.C. Liu, S. Yao and H.-Y. Chen, Modern Agrichem., 10, 27 (2011)..
- S. Ravi, K.M. Mathew, D. Padmanabhan, V.K.P. Unny and N. Sivaprasad, J. Labelled Comp. Radiopharm., 49, 339 (2006); doi:10.1002/jlcr.1048.
- K.D. Barnes, J.A. Dixson, and N. Murugesan, Herbicidal substituted benzoylsulfonamides, US5149357 A, 1990.
References
S.J. Koo, S.C. Ahn, J.S. Lim, S.H. Chae, J.S. Kim, J.H. Lee and J.H. Cho, Pestic. Sci., 51, 109 (1997); doi:10.1002/(SICI)1096-9063(199710)51:2<109::AID-PS585>3.0.CO;2-7.
2 K.T. Kim, B.B. Lee, G.H. Joe, et. al., Process for preparing 2, 6-di(4,6-dimethoxy pyrimidin-2-yl) oxybenzoic acid oxime ester derivatives as herbicides, Can. Pat. Appl., 2194080, 1997.
B. Kanrar and A. Bhattacharyya, J. Environ. Sci. Health B, 44, 788 (2009); doi:10.1080/03601230903238343.
Y. Nezu, M. Miyazaki, K. Sugiyama, N. Wada, I. Kajiwara and T. Miyazawa, Pestic. Sci., 47, 115 (1996); doi:10.1002/(SICI)1096-9063(199606)47:2<115::AID-PS397>3.0.CO;2-R.
C.U. Hur, J.H. Cho, S.M. Hong, H.W. Kim, Y.H. Lim, J.S. Rim, J.S. Kim and S.H. Chae, Pyrimidine Derivatives, Process for their Preparation and their Use as Herbicides, EP 658549 A1 (1995).
C. Luthy, H. Zondler, T. Rapold, G. Seifert, B. Urwyler, T. Heinis, H.C. Steinracken and J. Allen, Pest Manag. Sci., 57, 205 (2001); doi:10.1002/ps.304.
Z.G. Tian, A.C. Liu, S. Yao and H.-Y. Chen, Modern Agrichem., 10, 27 (2011)..
S. Ravi, K.M. Mathew, D. Padmanabhan, V.K.P. Unny and N. Sivaprasad, J. Labelled Comp. Radiopharm., 49, 339 (2006); doi:10.1002/jlcr.1048.
K.D. Barnes, J.A. Dixson, and N. Murugesan, Herbicidal substituted benzoylsulfonamides, US5149357 A, 1990.