95-02-3

Usage

Uses

Used in Pharmaceutical Industry:
4-AMINO-5-AMINOMETHYL-2-METHYLPYRIMIDINE, DIHYDROCHLORIDE is used as an intermediate in the synthesis of various pharmaceutical compounds due to its unique chemical structure and reactivity. Its ability to form stable complexes with other molecules makes it a valuable building block for the development of new drugs.
Used in Chemical Research:
In the field of chemical research, 4-AMINO-5-AMINOMETHYL-2-METHYLPYRIMIDINE, DIHYDROCHLORIDE serves as a versatile compound for studying the properties and reactions of aminopyrimidines. Its distinct structure allows researchers to explore its potential in various chemical reactions and applications, contributing to the advancement of scientific knowledge.
Used in Material Science:
4-AMINO-5-AMINOMETHYL-2-METHYLPYRIMIDINE, DIHYDROCHLORIDE can be utilized in material science for the development of novel materials with specific properties. Its ability to form complexes and interact with other molecules can be harnessed to create materials with tailored characteristics, such as improved stability, reactivity, or selectivity.
Used in Analytical Chemistry:
In analytical chemistry, 4-AMINO-5-AMINOMETHYL-2-METHYLPYRIMIDINE, DIHYDROCHLORIDE can be employed as a reagent or a reference compound for various analytical techniques. Its unique chemical properties make it suitable for use in assays, chromatography, and spectroscopy, among other methods, to enhance the accuracy and reliability of analytical results.

InChI:InChI=1/C6H10N4/c1-4-9-3-5(2-7)6(8)10-4/h3H,2,7H2,1H3,(H2,8,9,10)

Upstream product

• 23676-63-3 N-(4-amino-2-methyl-pyrimidin-5-ylmethyl)-acetamide 
• 98335-69-4 (4-amino-2-methyl-pyrimidin-5-yl)-acetic acid hydrazide 
• 698-29-3 2-methyl-4-amino-5-cyanopyrimidine 
• 23132-64-1 5-dimethylaminomethyl-2-methyl-pyrimidin-4-ylamine 
• 42981-14-6 2-(4-amino-2-methylpyrimidin-5-yl)acetamide 
• 7732-18-5 water 
• 70-16-6 Aneurin 
• 412277-96-4 4-amino-2-hydroxymethyl-pyrimidine-5-carbonitrile 
• 856972-79-7 6-chloro-5-dimethylaminomethyl-2-methyl-pyrimidin-4-ylamine 
• 220895-93-2 (4-amino-2-methyl-pyrimidin-5-yl)-acetic acid ethyl ester 
• 14273-76-8 ethyl 2-(4-chloro-2-methylpyrimidin-5-yl)acetate 
• 14273-42-8 (2-methyl-6-oxo-1,6-dihydro-pyrimidin-5-yl)-acetic acid ethyl ester 
• 175140-75-7 (4,6-dichloro-2-methyl-pyrimidin-5-yl)-acetic acid ethyl ester 
• 769-82-4 4-amino-5-methoxymethyl-2-methylpyrimidine 

Downstream Products

• 1886-34-6 2-methyl-4-amino-5-formylaminomethylpyrimidine 
• 31375-20-9 4-Amino-2-methyl-5-thioformamidomethylpyrimidin 
• 109439-49-8 acetic acid-[4-(7-methyl-1,2,3,4-tetrahydro-pyrimido[4,5-d]pyrimidin-2-yl)-anilide] 
• 1749-72-0 5-aminomethyl-2-methyl-3H-pyrimidin-4-one 
• 189745-28-6 5-(chloromethyl)-2-methyl-pyrimidin-4-amine 
• 31375-19-6 3,4-Dihydro-7-methylpyrimido<4,5-d>pyrimidine 
• 7403-34-1 7-methyl-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidine-2-thione 
• 874510-38-0 3-(4-amino-2-methyl-pyrimidin-5-ylmethyl)-4-hydroxy-4-phenyl-thiazolidine-2-thione 
• 875233-24-2 3-(4-amino-2-methyl-pyrimidin-5-ylmethyl)-5-(2-benzoyloxy-ethyl)-4-hydroxy-4-methyl-thiazolidine-2-thione 
• 299-35-4 3-(4-amino-2-methyl-pyrimidin-5-ylmethyl)-5-(2-hydroxy-ethyl)-4-methyl-3H-thiazole-2-thione 
• 490-82-4 thiamine thiazolone 
• 7066-07-1 Thiamin-thiazolon-O-acetat 
• 7275-24-3 3-(4-amino-2-methyl-pyrimidin-5-ylmethyl)-5-(2-chloro-ethyl)-4-methyl-thiazolium; chloride-hydrochloride 
• 59-43-8 vitamin B₁ 

Relevant academic research and scientific papers

Micro-reaction system and method for continuously preparing 2-methyl-4-amino-5-aminomethylpyrimidine by using same

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-aminomethylpyrimidine by using the micro-reaction system. The method comprises the following steps: modifying a Raney nickel catalyst by using formalin, filling a micro-channel reactor with the modified Raney nickel catalyst; simultaneously conveying hydrogen and a substrate solution containing both 2-methyl-4-amino-5-cyanopyrimidine and an alkaline agent into the micro-reaction system comprising a micro-mixerand the micro-channel reactor which communicate with each other in sequence; and carrying out a continuous catalytic hydrogenation reaction to obtain the 2-methyl-4-amino-5-aminomethylpyrimidine. Compared with the prior art, the method provided by the invention has the advantages that reaction time is only several minutes, the yield of the product 2-methyl-4-amino-5-aminomethylpyrimidine is greater than 99%, a technological process is continuous, an automation degree is high, space-time yield is high, operation is simple and convenient, the separation steps of reaction liquid and a catalyst is not needed, cost is low, and industrial production is easy.

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.

Preparation process of 2-methyl-4-amino-5-pyrimidinemethanamine

The invention discloses a preparation process of 2-methyl-4-amino-5-pyrimidinemethanamine. The preparation process of 2-methyl-4-amino-5-pyrimidinemethanamine comprises the following steps: 1) adding27-30 parts of DMF and 48-51 parts of dimethyl sulfate in a four-necked flask, heating to the temperature of 60-90 DEG C, insulating and stirring for 3-6 h, and then cooling; 2) adding 48-51 parts ofa methanol solution of sodium methylate, and after dropwise adding is finished, insulating and stirring for 5-15 min; 3) adding 27-30 parts of 3-aminopropionitrile, stirring for 30-60 min, and distilling under reduced pressure to obtain an intermediate 1; 4) then adding 130-150 parts of dichloromethane and stirring for 10-30 min, filtering, and distilling under reduced pressure to obtain an intermediate 2; and 5) adding 74-77 parts of a methanol solution of sodium methylate in the four-necked flask, cooling to the temperature of minus 5-5 DEG C, slowly adding 38-41 parts of acetamidine hydrochloride, insulating and stirring for 20-40 min, filtering, transferring to another flask and adding the intermediate 2 and 38-41 parts of NaOH, and stirring for 12-18 h after heating to obtain the final product. The preparation process of 2-methyl-4-amino-5-pyrimidinemethanamine is simple, and is low in pollution and low in raw material cost, and the yield of the product reaches up to 92.5%.

2-methyl-4-amino-5 - (aminomethyl) method for the preparation of pyrimidine

The invention discloses a preparation method of 2-methyl-4-amino-5-(aminomethyl) pyrimidine. The preparation method is characterized by comprising the following steps: in the presence of an alkaline agent, contacting 2-methyl-4-amino-5-(formamide methyl) pyrimidine with methanol to react, wherein the weight ratio of the amount of the alkaline agent to the amount of the 2-methyl-4-amino-5-(formamide methyl) pyrimidine is (0.001-0.05) to 1. According to the method provided by the invention, a great deal of organic salts, inorganic salts and liquid waste are not produced, and byproducts as well as the residual methanol can be completely recycled. The preparation method is economical, environmentally friendly and capable of meeting the development requirements of the existing national energy-saving environmental-protection industrial economy. Besides, the preparation method provided by the invention is simple to operate, easily available in raw material and suitable for the requirements of the industrial production. Moreover, the product is easy to separate and purify.

One-step ring preparation of 2-methyl-4-amino-5-amino methyl pyrimidine convenient synthetic method

The invention relates to a portable synthesis method for preparing 2-methyl-4-amino-5-aminoethylpyrimidine through one-step cyclization reaction. The method comprises the following steps: directly catalyzing acetamidine hydrochloride and 3-acyl aminopropionitrile to condense and to react with triester orthoformate for dealcoholization and cyclization by using lewis acid, and then hydrolyzing to obtain a vitamin B1 key intermediate, namely the 2-methyl-4-amino-5-aminoethylpyrimidine. According to the method disclosed by the invention, the raw materials are low in cost and easily obtained, and no sodium alcoholate needs to be used for dissociating acetamidine hydrochloride, thus the decomposition of acetamidine is reduced, and the high yield is achieved through reaction; the cyclization and hydrolysis reactions are sequentially carried out, products in all steps are not required to be separated and purified, and the synthesis method is simple and convenient to operate. Highly carcinogenic o-chloroaniline or other micromolecular aniline compounds are not used, and the portable synthesis method is environment-friendly in process, free of production of wastewater and beneficial to industrial production.

Vitamin B1 key intermediate 2-methyl-4-amino-5-amino methyl pyrimidine method for preparing environmental protection of

The invention relates to an environment-friendly preparation method for a key intermediate 2-methyl-4-amino-5-aminomethyl pyrimidine of vitamin B1. The method comprises the following steps: substituting highly oncogenic o-chloroaniline or other micromolecular aniline derivatives with a functional polymer containing an aromatic amine structural unit; carrying out a condensation reaction with enol alkali under an acidic condition so as to produce a corresponding enamine polymer; subjecting the enamine polymer and ethanamidine hydrochloride to condensation so as to produce 2-methyl-4-amino-5-formylamino-pyrimidine; and carrying out hydrolysis so as to prepare 2-methyl-4-amino-5-aminomethyl pyrimidine; wherein the functional polymer containing the aromatic amine structural unit is released at the same time and is cyclically used for next batch of reactions. The method has short process flow, discharges a small amount of waste water and waste liquid and is beneficial for industrial production and for improvement of the industrial production level of vitamin B1.

Design, synthesis and molecular docking of amide and urea derivatives as Escherichia coli PDHc-E1 inhibitors

By targeting the ThDP binding site of Escherichia coli PDHc-E1, two new 'open-chain' classes of E. coli PDHc-E1 inhibitors, amide and urea derivatives, were designed, synthesized, and evaluated. The amide derivatives of compound 6d, with 4-NO2 in the benzene ring, showed the most potent inhibition of E. coli PDHc-E1. The urea derivatives displayed more potent inhibitory activity than the corresponding amide derivatives with the same substituent. Molecular docking studies confirmed that the urea derivatives have more potency due to the two hydrogen bonds formed by two NH of urea with Glu522. The docking results also indicate it might help us to design more efficient PDHc-E1 inhibitors that could interact with Glu522.

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.

Lewis acid-catalyzed synthesis of 4-aminopyrimidines: A scalable industrial process

Pyrimidine synthesis starting from acrylonitrile has been known since the 1960s. The new Lewis acid-catalyzed condensation reaction allows the synthesis of 4-aminopyrimidines starting from the easily accessible chemical acrylonitrile without the need for carcinogenic chemicals and costly derivatization in up to 90% yield. The method is versatile and applicable for industrial-scale synthesis of biologically relevant substances such as vitamin B1 and trimethoprim.