16849-88-0

Usage

Uses

Used in Pharmaceutical Industry:
[(Dimethylamino)methylene]malononitrile is used as an intermediate in the synthesis of pharmaceutical compounds for its ability to react with a range of other molecules, facilitating the development of new drugs with potential therapeutic applications.
Used in Chemical Industry:
In the chemical industry, [(Dimethylamino)methylene]malononitrile is used as a reagent in the production of various organic compounds, such as dyes, pigments, and polymers, due to its reactive nature and compatibility with different chemical processes.
Used in Agrochemical Industry:
[(Dimethylamino)methylene]malononitrile is employed as a key component in the development of agrochemicals, including pesticides and herbicides, as its chemical properties enable the creation of effective and targeted compounds for agricultural use.
Used in Material Science:
(DIMETHYLAMINOMETHYLENE)MALONONITRILE is also used as a building block in the field of material science, where it contributes to the development of advanced materials with specific properties, such as conductivity, magnetism, or optical characteristics, for various applications in electronics, energy, and other industries.

Synthesis Reference(s)

Journal of the American Chemical Society, 97, p. 800, 1975 DOI: 10.1021/ja00837a020

InChI:InChI=1/C6H7N3/c1-9(2)5-6(3-7)4-8/h5H,1-2H3

Upstream product

• 5763-87-1 N,N-dimethylvinylamine 
• 997-76-2 tricyanoethene 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 672-25-3 aminomethylene-malononitrile 
• 124-40-3 dimethyl amine 
• 68-12-2 N,N-dimethyl-formamide 
• 109-77-3 malononitrile 
• 1188-33-6 N,N-dimethylformamide diethyl diacetal 
• 758-16-7 N,N-dimethylthioformamide 
• 35520-41-3 trans-3-dimethylaminoacrylonitrile 
• 2950-43-8 hydroxylamine-O-sulfonic acid 
• 107-91-5 cyanoacetic acid amide 
• 21511-55-7 (methoxymethylidene)dimethylammonium methyl sulfate 
• 3724-43-4 Vilsmeier reagent 

Downstream Products

• 255389-59-4 7-amino-1-methylpyrazolo[1,5-a]pyrimidine-6-carbonitrile 
• 698-29-3 2-methyl-4-amino-5-cyanopyrimidine 
• 28524-64-3 7-amino-[1,2,4]triazolo[1,5-a]pyrimidine-6-carbonitrile 
• 21787-04-2 4-iminopyrimido[2,1-b]benzothiazol-3-carbonitrile 
• 78415-72-2 1,6-dihydro-2-methyl-6-oxo-(3,4'-bipyridine)-5-carbonitrile 
• 14918-98-0 2-((benzylamino)methylene)malononitrile 
• 89712-07-2 2-cyano-3-dimethylamino-thioacrylamide 

Relevant academic research and scientific papers

Synthesis and Antiviral Bioactivity of Novel 2-Substituted Methlthio-5-(4-Amino-2-Methylpyrimidin-5-yl)-1,3,4-Thiadiazole Derivatives

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.

Hydrogenation of imino-bisnitriles - Synthesis of novel triamines

The hydrogenation of iminonitriles and iminobisnitriles of type 1a-f is a particularly difficult process as the intermediate dieneamines are highly susceptible to addition reactions. A short general method of preparation and purification of 2-aminomethylene-1,3-diamine of type 2a-e by catalytic hydrogenation of iminobisnitriles is described. Copyright Taylor & Francis Group, LLC.

Fully Continuous Flow Synthesis of 5-(Aminomethyl)-2-methylpyrimidin-4-amine: A Key Intermediate of Vitamin B1

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.

Fully continuous flow preparation method of 2-methyl-4-amino-5-aminomethylpyrimidine

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.

Method for continuously preparing (dimethylamine methylene)malononitrile by using micro-reaction system

The invention discloses a method for continuously preparing (dimethylamine methylene)malononitrile by using a micro-reaction system. The method comprises the steps of respectively and simultaneously pumping a solution obtained by mixing cyanoacetamide, N,N-dimethylformamide and a catalyst and phosphorus oxychloride into a micro-reaction system comprising a first micro-mixer and a micro-channel reactor which are communicated with each other, and carrying out continuous catalytic dehydration condensation reaction; after the pH value of the crude product mixed solution is adjusted, carrying out continuous liquid-liquid extraction separation on the crude product mixed solution in a centrifugal extraction unit composed of a plurality of annular space type centrifugal extractors connected in series by using an organic solvent, collecting an extraction phase to obtain the target product (dimethylamine methylene)malononitrile. Compared with the prior art, the method has the advantages that thereaction can be safely carried out at normal temperature, the reaction time is short, the product yield is greater than 95%, the efficiency of the technological process is high, the energy consumption is low, and the method has a good industrial application prospect.

Synthesis and fungicidal activity of novel 1,2,4-triazole derivatives containing a pyrimidine moiety

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).

METHODS OF LOWERING PROPROTEIN CONVERTASE SUBTILISIN/KEXIN TYPE 9 (PCSK9)

The invention relates to new methods of modulating cholesterol by inhibiting proprotein convertase subtilisin/kexin type 9 (PCSK9) with fatty acid derivatives; and new methods for treating or preventing a metabolic disease comprising the administration of an effective amount of a fatty acid derivative. The present invention is also directed to fatty acid bioative derivatives and their use in the treatment of metabolic diseases.

Development of two scalable syntheses of 4-amino-5-aminomethyl-2- methylpyrimidine: Key intermediate for vitamin b1

Two scalable processes for the synthesis of 4-amino-5-aminomethyl-2- methylpyrimidine (2) are described. In the first approach, the less expensive 2-cyanoacetamide was reacted with Vilsmeier reagent to afford enamine 18, followed by the condensation with acetamidine to produce the 4-amino-2-methylpyrimidine-5-carbonitrile (6); subsequent hydrogenation gave 2 in 65% overall yield. In the second approach, malononitrile was treated with the ionic salt 21, prepared in situ from DMF and dimethyl sulfate, to give 18, which, without isolation was reacted with acetamidine hydrochloride to afford the common intermediate 6. Overall yield of this approach was 70%. Both methods are performed in a convenient manner suitable for industrial use.

METHOD FOR PREPARATION OF 2-METHYL-4-AMTNO-5-CYANOPYRIMIDINE

Disclosed is a method for preparation of 2-methyl-4-amino-5-cyanopyrimidine (I). The present method comprises the steps of reacting cyanoacetamide with formamide derivatives in the presence of various acyl halides and catalysts to produce compound (II), and condensing the compound (II) with acetamide hydrochloride in the present of a base to obtain 2-methyl-4-amino-5-cyanopyrimidine (I).

PROCESS FOR PREPARING 2-METHYL-4-AMINO-5-CYANOPYRIMIDINE

A process for synthesizing 2-methyl-4-amino-5-cyanopyrimidine is provided. It is characterized by reacting malononitrile with an ionic salt compound (III) in a certain solvent under the effect of an alkali, and condensing the product thereof without separation directly with ethanamidine hydrochloride to form a ring in the presence of an alkali, so as to prepare 2-methyl-4-amino-5-cyanopyrimidine (I).