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An Efficient and Convenient Synthesis of 4,6-Dichloro-2-methyl-5-nitropyrimidine
Corresponding Author(s) : Defeng Xu
Asian Journal of Chemistry,
Vol. 26 No. 12 (2014): Vol 26 Issue 12
Abstract
A convenient synthesis of 4, 6-dihydro-2-methyl-pyrimidine can be obtained by cyclization reaction of acetamidine hydrochloride and diethyl malonate in the presence of sodium methoxide for a 91.2 % yield. 4, 6-Dihydro-2-methyl-5-nitropyrimidine can be achieved by nitration under the mixed acids of nitric acid, trichloroacetic acid and acetic acid in an 88.3 % yield and then the chlorination using phosphorus oxytrichloride can afford 4, 6-dichloro-2-methyl-5-nitropyrimidine with an 82.6 % yield.
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- S.A. Palkhiwala, A. Yu and W.H. Frishman, Heart Dis., 2, 83 (2000).
- N.R. Kotagale, S.J. Tripathi, M.M. Aglawe, C.T. Chopde, M.J. Umekar and B.G. Taksande, Pharmacol. Biochem. Behav., 107, 42 (2013).
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- O.K. George, R.R. Gonzalez Jr. and L.P. Edwards, J. Cardiovasc. Pharmacol., 43, 306 (2004).
- A. Itai, I. Carmen, N. Vladimir, K. Eyal, Polymorphs of Moxonidine and Processes for Preparation therefore, EP1894926 A1 (2008).
- K. Kazutoshi, M. Kiyoshi and O. Shuhei, Preparation of Pyrimidine Derivatives as ACAT Inhibitors and Pharmaceutical Compositions Containing them, EP 561175 A1 (1993).
- B. Werner, E. Franz, H. Ulrich and S. Helmut, Feed Additive for Improving Growth in Agricultural Animals, US4853402 A1 (1989).
- J.N. Ashley, J.O. Harris, C.E. Dalgliesh, E.F.M. Stephenson, A. Albert, D. Magrath, J. Baddiley, A. Topham and R.A. Reed, J. Chem. Soc., 678 (1944).
- M.H. Norman, N. Chen, Z.D. Chen, C. Fotsch, C. Hale, N. Han, R. Hurt, T. Jenkins, J. Kincaid, L. Liu, Y. Lu, O. Moreno, V.J. Santora, J.D. Sonnenberg and W. Karbon, J. Med. Chem., 43, 4288 (2000).
- A. Albert, D.J. Brown and H.C.S. Wood, J. Chem. Soc., 5, 3832 (1954).
- A.A. Astrat'ev, D.V. Dashko, A.Y. Mershin, A.I. Stepanov and N.A. Urazgil'deev, Russ. J. Org. Chem., 37, 729 (2001).
References
S.A. Palkhiwala, A. Yu and W.H. Frishman, Heart Dis., 2, 83 (2000).
N.R. Kotagale, S.J. Tripathi, M.M. Aglawe, C.T. Chopde, M.J. Umekar and B.G. Taksande, Pharmacol. Biochem. Behav., 107, 42 (2013).
S. Deftereos, G. Giannopoulos, C. Kossyvakis, M. Efremidis, V. Panagopoulou, K. Raisakis, A. Kaoukis, S. Karageorgiou, G. Bouras, A. Katsivas, V. Pyrgakis and C. Stefanadis, Am. J. Cardiol., 112, 684 (2013).
O.K. George, R.R. Gonzalez Jr. and L.P. Edwards, J. Cardiovasc. Pharmacol., 43, 306 (2004).
A. Itai, I. Carmen, N. Vladimir, K. Eyal, Polymorphs of Moxonidine and Processes for Preparation therefore, EP1894926 A1 (2008).
K. Kazutoshi, M. Kiyoshi and O. Shuhei, Preparation of Pyrimidine Derivatives as ACAT Inhibitors and Pharmaceutical Compositions Containing them, EP 561175 A1 (1993).
B. Werner, E. Franz, H. Ulrich and S. Helmut, Feed Additive for Improving Growth in Agricultural Animals, US4853402 A1 (1989).
J.N. Ashley, J.O. Harris, C.E. Dalgliesh, E.F.M. Stephenson, A. Albert, D. Magrath, J. Baddiley, A. Topham and R.A. Reed, J. Chem. Soc., 678 (1944).
M.H. Norman, N. Chen, Z.D. Chen, C. Fotsch, C. Hale, N. Han, R. Hurt, T. Jenkins, J. Kincaid, L. Liu, Y. Lu, O. Moreno, V.J. Santora, J.D. Sonnenberg and W. Karbon, J. Med. Chem., 43, 4288 (2000).
A. Albert, D.J. Brown and H.C.S. Wood, J. Chem. Soc., 5, 3832 (1954).
A.A. Astrat'ev, D.V. Dashko, A.Y. Mershin, A.I. Stepanov and N.A. Urazgil'deev, Russ. J. Org. Chem., 37, 729 (2001).