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The New Synthetic Process of Adenine

Author: HuangZuo
Tutor: WangKai
School: Wuhan Institute of Technology
Course: Biochemical Engineering
Keywords: adenine technology research synthesis one pot ethyl malonate
CLC: TQ464.6
Type: Master's thesis
Year: 2013
Downloads: 82
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Abstract


This Thesis is based on the synthesis process of adenine(1), which is aimed to obtain amore pure end product and to improve conditions with one completely new approach thatis based on the principle of drug synthesis design and document to the synthesis of (1).Adenine is one of the important organic compounds, which is well known for living organisms. It is also an intermediate of many pharmaceutical raw materials, such as vitamin B4, plant hormone, adefovir ester and other pharmaceutical raw materials. Therefore, adenine process research has the very vital significance.Specific synthetic approach can be described as follows:Firstly, using (7) as the starting material, the intermediate4,6-dihydroxy pyridine(6) was prepared through cyclization adding formamide with alkaline condition. Secondly, using nitric acid nitration to obtain4,6-dihydroxy-5-nitro pyridine(5), and then, under the condition of organic alkali as catalyst, using phosphorus oxychloride aschloride for intermediate of4,6-dichloro-5-nitro pyridine(4), and fourth, using Fe/HAc as reduction system, nitro being reducted into amino to obtain intermediate4,6-dichloro-5-amino pyrimidine(3), and finally, by “one pot”, under alkaline conditions,adding formamide by cyclization and ammonolysis directly to obtain adenine(1). The author has conducted the five-step reaction process improvements, and has obtained the most appropriate process through experiment. The total yield of the five steps is30.1%. The physical parameters of intermediate (6)、(5)、(4)、(3) and (1) is similar to that of the references, and adenine(1) have been confirmed by1H NMR、IR and MS.The key technology of adenine’s synthesis is how to convert intermediate(3) intoadenine by cyclization and ammonolysis using the method of “one pot”. The innovation is also the synthetic route of intermediate(3) to adenine(1). The synthetic route which effectively reduced the material cost and simplified operation has potentialindustrial value.

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CLC: > Industrial Technology > Chemical Industry > Pharmaceutical chemical industry > Drug production of biological products > Nucleic acid
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