1886-34-6

Usage

Uses

Used in Pharmaceutical Industry:
4-Amino-5-(formamidomethyl)-2-methylpyrimidine is used as an intermediate compound for the synthesis of various pharmaceutical products. Its role in the metabolism of thiamine makes it a valuable component in the development of drugs targeting carbohydrate metabolism and nerve function-related disorders.
Used in Nutritional Supplements:
As a metabolite of thiamine, 4-Amino-5-(formamidomethyl)-2-methylpyrimidine is used in the formulation of nutritional supplements designed to support carbohydrate metabolism and overall nerve health. These supplements can be particularly beneficial for individuals with thiamine deficiencies or those requiring additional support for their metabolic and nerve functions.
Used in Research and Development:
4-AMino-5-(forMaMidoMethyl)-2-MethylpyriMidine is also utilized in research and development for understanding the role of thiamine in cellular processes, as well as for the development of new therapeutic strategies targeting carbohydrate metabolism and nerve function. Researchers can use 4-Amino-5-(formamidomethyl)-2-methylpyrimidine to study the mechanisms of thiamine action and its impact on human health.
Used in Diagnostic Applications:
4-Amino-5-(formamidomethyl)-2-methylpyrimidine can be employed in the development of diagnostic tools and tests to measure thiamine levels in the body. This can help in the early detection of thiamine deficiencies and the monitoring of treatment efficacy for related health conditions.

InChI:InChI=1/C7H10N4O/c1-5-10-3-6(2-9-4-12)7(8)11-5/h3-4H,2H2,1H3,(H,9,12)(H2,8,10,11)

Upstream product

• 64-18-6 formic acid 
• 95-02-3 5-(aminomethyl)-2-methylpyrimidin-4-amine 
• 31375-20-9 4-Amino-2-methyl-5-thioformamidomethylpyrimidin 
• 7732-18-5 water 
• 119206-80-3 α-phenyl-aminomethylene-β-formylaminopropionitrile 
• 143-37-3 acetamidine 
• 124-42-5 acetamidine hydrochloride 
• 106030-08-4 α-formyl-β-formylaminopropionitrile sodium salt 
• 75-05-8 acetonitrile 
• 698-29-3 2-methyl-4-amino-5-cyanopyrimidine 
• 109-94-4 formic acid ethyl ester 
• 77287-34-4 formamide 
• 175140-75-7 (4,6-dichloro-2-methyl-pyrimidin-5-yl)-acetic acid ethyl ester 
• 14273-42-8 (2-methyl-6-oxo-1,6-dihydro-pyrimidin-5-yl)-acetic acid ethyl ester 

Downstream Products

• 31375-20-9 4-Amino-2-methyl-5-thioformamidomethylpyrimidin 
• 67-03-8 Thiamine hydrochloride 
• 95-02-3 5-(aminomethyl)-2-methylpyrimidin-4-amine 
• 141-53-7 sodium formate 
• 70732-86-4 thiamine hydrochloride 
• 109653-94-3 3-(4-amino-2-methyl-pyrimidin-5-ylmethyl)-5-(2-hydroxy-ethyl)-4-phenyl-thiazolium; chloride-hydrochloride 
• 7275-24-3 3-(4-amino-2-methyl-pyrimidin-5-ylmethyl)-5-(2-chloro-ethyl)-4-methyl-thiazolium; chloride-hydrochloride 

Relevant academic research and scientific papers

Synthesis method of formyl pyrimidine

The invention discloses a synthesis method of formyl pyrimidine, which comprises the following steps: (1) by using formamide and acrylonitrile as raw materials, carrying out Michael addition reactionunder the action of a catalyst A and post-treatment to obtain 3-formamide propionitrile; (2) by taking 3-formamido propionitrile and paraformaldehyde as raw materials, carrying out condensation reaction in the presence of a catalyst B and a benzene solvent, and carrying out post-treatment to obtain N-(2-cyanovinyl)-formamide; and (3) with N-(2-cyanovinyl)-formamide and free acetamidine as raw materials, carrying out a condensation reaction in a low-grade fatty alcohol solvent, then heating, carrying out oxidative aromatization under the action of a catalyst C, and finally, carrying out post-treatment to obtain formyl pyrimidine. The synthesis method disclosed by the invention has the advantages that the route is green, safe and environment-friendly; and an activating group and a leaving group are not adopted, so that the atom economy of the reaction is high.

Method for synthesizing 2-methyl-4-amino-5-formamide methyl pyrimidine

The invention discloses a method for synthesizing 2-methyl-4-amino-5-formamide methyl pyrimidine. The method comprises the following steps: conveying an organic ester solvent solution with beta-aminopropionitrile and an organic alcohol solution with sodium alcoholate into a pipeline reactor, performing a continuous reaction, discharging the materials, performing cooling, performing neutralizationto neutral, performing vacuum recycling on a solvent, continuously adding methylbenzene, and performing water washing so as to obtain a methylbenzene solution of 2-formyl-3-formyl amino-propionitrile;adding acetamidine hydrochloride into the organic alcohol solution with sodium alcoholate, performing filtration after addition, collecting filtrate, performing heating, putting the methylbenzene solution of 2-formyl-3-formyl amino-propionitrile; and adding acetamidine hydrochloride into the filtrate, under a vacuum condition, evaporating out the solvent and adding an alcohol of a corresponding volume at the same time, stopping the reaction when a solution of a volume equal to that of the organic alcohol solution with the sodium alcoholate is evaporated out, performing neutralization to neutral, performing vacuum crystallization, performing filtering, and performing drying, so as to obtain the compound. The method is simple, gentle in reaction condition, low in reaction equipment requirement, low in cost and high in yield.

Synthetic method of 2-methyl-4-amino-5-formyl aminomethylpyrimidine

The invention relates to a synthetic method of 2-methyl-4-amino-5-formyl aminomethylpyrimidine. The method comprises the following steps: a benzene solvent and a solid acid catalyst are added to a reaction flask and stirred, alpha-sodio formyl-beta-formyl aminopropionitrile is added, heating is performed, an acetamidine hydrochloride solution dissolved in an alcohol solvent is added dropwise, a thermal reaction and filtering are performed, the solid acid catalyst is recovered and treated for recycling, and a filtrate is a 2-methyl-4-amino-5-formyl aminomethylpyrimidine solution. O-chloroaniline as a raw material used in the traditional synthetic process is not used, 2-methyl-4-amino-5-formyl aminomethylpyrimidine is directly synthesized from alpha-sodio formyl-beta-formyl aminopropionitrile and acetamidine hydrochloride under the action of the solid acid catalyst, intermediate processes are omitted, the method is an environment-friendly process because the solid acid catalyst is recyclable, and trace cancerogen residues in a vitamin B1 product are avoided; synthesis yield is high, and the requirement for current green development is met.

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.

Novel synthesis of substituted 4-amino-pyrimidines

The present invention is directed to a process for the manufacture of compounds of formula IV wherein R1 is an amino protecting group, and R2 is hydrogen or C1-10 alkyl, comprising a) reacting a compound of formula Ia, wherein M+ is a cation, preferably selected from the group consisting of Li+, Na+, K+, 1/2 Mg2+ and 1/2 Zn2+, (formula 1a) with an ammonium salt NH4+X-, wherein X- is an anion, preferably selected from the group consisting of chloride, bromide, sulfate and acetate, in a solvent to a compound of formula II b) reacting a compound of formula II with a nitrile R2-CN in the presence of a base to a compound of formula IV. The present invention is further directed to compounds of formula II and their use for the manufacture of vitamin B1.

SYNTHESIS OF 4-AMINO-PYRIMIDINES

Process for the manufacture of a compound of the structure (I) with R1 = hydrogen, alkyl (C1 - C10, linear, cyclic or branched, aliphatic or aromatic), NR'R (wherein R' and R are independently selected from H, alkyl [C1 - C10, linear, cyclic or branched, aliphatic or aromatic] and R2 = CH2R3 wherein R3 is selected from NHR1 ' (with R ' = C(O)H, C(O)CH3, C(O)alkyl, CH2C6H2(OMe)3 or other saponifiable residues), alkyl (C1 - C10, linear, cyclic or branched) aromatic residues, heteroaryl residues, substituted aryl residues, e. g. 3,4,5-trimethoxy-phenyl) wherein 1 equivalent of an α-formyl-propionitrile salt is reacted with 0.75 to 2 equivalents of an acetamidine salt in the presence of a Lewis acid.

α-(o-chlorophenyl)-aminomethylene-β-formylaminopropionitrile

α-(o-Chlorophenyl)-aminomethylene-β-formylaminopropionitrile, process for its preparation by reacting a metal salt of α-formyl-β-formylaminopropionitrile with a salt of o-chloroaniline in an aqueous medium, and use of the product to prepare the compound of the formula STR1 by reaction with acetamidine. The pyrimidine thus obtained is an intermediate for the preparation of vitamin B1.

α-Aminomethylene-β-formylaminopropionitrile and its manufacture

An improved method of manufacture of 2-methyl-4-amino-5-formylaminomethylpyrimidine (II), wherein a N-substituted or unsubstituted α-aminomethylene-β-formylaminopropionitrile (I) is reacted with acetamidine. Compound II is an intermediate for the manufacture of vitamin B1.