698-29-3Relevant articles and documents
Fully continuous flow preparation method of 2-methyl-4-amino-5-aminomethylpyrimidine
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Paragraph 0006; 0045-0046; 0048-0061, (2021/07/17)
The invention discloses a fully continuous flow preparation method of 2-methyl-4-amino-5-aminomethylpyrimidine. The method comprises the following steps: mixing a mixed solution of cyanoacetamide, N, N-dimethylformamide and a catalyst with phosphorus oxychloride in a micro-mixer, and carrying out a continuous flow reaction in a micro-channel reactor to obtain (dimethyl aminomethylene) malononitrile; continuously quenching, continuously extracting and separating, concentrating an organic solution, mixing with a methanol solution, and continuously reacting with organic alkali to obtain 2-methyl-4-amino-5-cyanopyrimidine; continuously filtering the reaction mixed solution, dissolving the solid with methanol, conveying the dissolved solid and hydrogen to a fixed bed microchannel reactor through a micromixer, carrying out hydrogenation reaction, and concentrating, drying and purifying the product to obtain the 2-methyl-4-amino-5-aminomethylpyrimidine product. The method is mild in reaction condition, short in reaction time, high in product yield, low in energy consumption, green, safe and easy to industrially amplify and apply.
Micro-reaction system and method for continuously preparing 2-methyl-4-amino-5-cyanopyrimidine by using same
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Paragraph 0016; 0075-0104, (2021/05/29)
The invention belongs to the technical field of pharmaceutical engineering, and particularly relates to a micro-reaction system and a method for continuously preparing 2-methyl-4-amino-5-cyanopyrimidine by using the micro-reaction system. The preparation method comprises the following steps: respectively and simultaneously pumping an acetamidine hydrochloride solution and a (dimethyl aminomethylene) malononitrile solution into a micro-reaction system comprising a micro-mixer and an oscillating micro-channel reactor which are communicated in sequence, and carrying out a continuous condensation cyclization reaction to obtain the 2-methyl-4-amino-5-cyanopyrimidine. Compared with the prior art, the method has the advantages that the reaction time is shortened to be within 30 minutes, side reactions are inhibited to the maximum extent, the yield of the product 2-methyl-4-amino-5-cyanopyrimidine is increased to 90% or above, operation is easy and convenient, the technological process is continuous, the automation degree is high, the space time yield is high, energy consumption is greatly reduced, cost is low, and industrial application is easy.
Fully Continuous Flow Synthesis of 5-(Aminomethyl)-2-methylpyrimidin-4-amine: A Key Intermediate of Vitamin B1
Chen, Fener,Huang, Huashan,Jiang, Meifen,Liu, Minjie
, p. 2331 - 2337 (2021/10/25)
Herein, we demonstrate an expeditiously fully continuous flow synthesis of 5-(aminomethyl)-2-methylpyrimidin-4-amine, a key intermediate for vitamin B1. The process is accomplished via three chemical transformations in six sequential continuous flow devices from an economical starting material, 2-cyanoacetamide. First, single step continuous flow synthesis is demonstrated in a certain type of flow reactor for each reaction step, with a yield of 94, 90, and 99%, respectively. Then, fully continuous flow synthesis of 5-(aminomethyl)-2-methylpyrimidin-4-amine is demonstrated in 84% total yield with a total residence time of 74 min and 0.92 g/h throughput.
Synthesis and fungicidal activity of novel 1,2,4-triazole derivatives containing a pyrimidine moiety
Wu, Wen-Neng,Jiang, Yang-Ming,Fei, Qiang-,Du, Hai-Tang
, p. 1171 - 1175 (2019/07/05)
A series of novel 1,2,4-triazole derivatives containing a pyrimidine moiety were synthesized and their fungicidal activities were evaluated. The preliminary biological test indicated that some of the target compounds exhibited moderate to good fungicidal activities against the tested plant pathogenic fungi compared with the commercial agent. Among them, compounds 9n and 9o exhibited excellent antifungal activity against Phompsis sp., with the half-maximal effective concentration (EC50) values of 25.4 and 31.6 μg/mL, which were even better than the commercial agent of Pyrimethanil (32.1 μg/mL). Meanwhile, compound 9o showed better fungicidal activities against B. dothidea and B. cinerea with 40.1 and 55.1 μg/mL, respectively, in comparison with that of commercial Pyrimethanil (57.6 and 62.8 μg/mL).
Design and optimization of N-acylhydrazone pyrimidine derivatives as E. coli PDHc E1 inhibitors: Structure-activity relationship analysis, biological evaluation and molecular docking study
He, Haifeng,Xia, Hongying,Xia, Qin,Ren, Yanliang,He, Hongwu
, p. 5652 - 5661 (2017/10/09)
By targeting the thiamin diphosphate (ThDP) binding site of Escherichia coli (E. coli) pyruvate dehydrogenase multienzyme complex E1 (PDHc E1), a series of novel ‘open-chain’ classes of ThDP analogs A, B, and C with N-acylhydrazone moieties was designed and synthesized to explore their activities against E. coli PHDc E1 in vitro and their inhibitory activity against microbial diseases were further evaluated in vivo. As a result, A1–23 exhibited moderate to potent inhibitory activities against E. coli PDHc E1 (IC50 = 0.15–23.55 μM). The potent inhibitors A13, A14, A15, C2, had strong inhibitory activities with IC50 values of 0.60, 0.15, 0.39 and 0.34 μM against E. coli PDHc E1 and with good enzyme-selective inhibition between microorganisms and mammals. Especially, the most powerful inhibitor A14 could 99.37% control Xanthimonas oryzae pv. Oryzae. Furthermore, the binding features of compound A14 within E. coli PDHc E1 were investigated to provide useful insights for the further construction of new inhibitor by molecular docking, site-directed mutagenesis, and enzymatic assays. The results indicated that A14 had most powerful inhibition against E. coli PDHc E1 due to the establishment of stronger interaction with Glu571, Met194, Glu522, Leu264 and Phe602 at active site of E.coli PDHc E1. It could be used as a lead compound for further optimization, and may have potential as a new microbicide.
Method for preparing 2-methyl-4-amino-5-cyanopyrimidine by Mannich reaction
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Paragraph 0041; 0042; 0043; 0044; 0045; 0046; 0047-0052, (2017/08/25)
The invention relates to a method for preparing 2-methyl-4-amino-5-cyanopyrimidine by Mannich reaction. According to the invention, ethylamidine hydrochloride, malononitrile and an aldehyde compound are used as raw materials and subjected to the Mannich reaction to obtain 2-methyl-4-amino-5-cyano-5,6-dihydropyrimidine hydrochloride that is then oxidized by an oxidizer to obtain the 2-methyl-4-amino-5-cyanopyrimidine. The raw materials malononitrile and ethylamidine hydrochloride used for the method for preparing 2-methyl-4-amino-5-cyanopyrimidine by Mannich reaction are high in stability under reaction conditions, thereby reducing side reactions of the malononitrile and free ethylamidine hydrochloride under an alkaline condition and providing guarantee for high yield and high purity of the product.
cGAS ANTAGONIST COMPOUNDS
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Paragraph 0280, (2017/11/06)
Disclosed are novel compounds of Formula (I) that are cGAS antagonists, methods of preparation of the compounds, pharmaceutical compositions comprising the compounds, and their use in medical therapy.
A vitamin B1 key intermediate 2-methyl-4-amino-5-cyano-pyrimidine simple method for preparing (by machine translation)
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Paragraph 0058-0059, (2017/01/23)
The invention relates to a vitamin B1 key intermediate 2-methyl-4-amino-5-cyano-pyrimidine simple method for preparing. This invention utilizes the original which is cheap and easy to obtain three of acetic acid as the starting material, and sequentially 3-aminopropionitrile, melamine condensation, condensation in the molecular under alkaline conditions into the annular, oxidation to prepare 2-methyl-4-amino-5-cyano-pyrimidine. One-pot synthesis completion of reaction steps. The method of the present invention easy availability of raw materials, gentlely conditions, reaction selectivity, high-purity high-yield, small amount of waste water, the product cost is low. (by machine translation)
CYCLIC AMINOMETHYL PYRIMIDINE DERIVATIVE
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Paragraph 0274-0276, (2016/06/01)
The present invention provides a cyclic aminomethyl pyrimidine derivative and a pharmaceutically acceptable salt thereof with high selectivity for dopamine D4 receptors, which are useful for treating a disease such as attention deficit hyperactivity disorder. Specifically, a compound of formula (1) or a pharmaceutically acceptable salt thereof is provided, wherein n and m are independently 1 or 2; Ra is C1-6 alkyl group, C3-6 cycloalkyl group, or amino group; Rb is hydrogen atom, C1-6 alkyl group or the like, provided that when Ra is amino group, then Rb is hydrogen atom; Rc1 and Rc2 are independently hydrogen atom, or C1-6 alkyl group; Rd1 and Rd2 are independently hydrogen atom, fluorine atom or the like; ring Q is an optionally-substituted pyridyl group or an optionally-substituted isoquinolyl group; and the bond having a dashed line is a single or double bond.
Synthesis and Antiviral Bioactivity of Novel 2-Substituted Methlthio-5-(4-Amino-2-Methylpyrimidin-5-yl)-1,3,4-Thiadiazole Derivatives
Wu, Wen-Neng,Tai, An-Qi,Chen, Qin,Ouyang, Gui-Ping
, p. 626 - 632 (2016/04/19)
A series of novel 2-substituted methlthio-5-(4-amino-2-methylpyrimidin-5-yl-)-1,3,4-thiadiazole derivatives were synthesized, characterized and evaluated for antiviral activities against tobacco mosaic virus (TMV). The preliminary biological results indicated that most compounds exhibit excellent antiviral activity against TMV in vivo. Among these compounds, compounds 9c, 9i, and 9p displayed the similar curative effect against TMV (EC50 = 287.05-322.47 μg/mL) to that of the commercial agent Ningnanmycin (EC50 = 301.83 μg/mL). In particular, compound 9d demonstrated the best curative effect against TMV (EC50 = 266.21 μg/mL), which was better than that of commercial Ningnanmycin.
