1886-34-6

Basic information

• Product Name: 4-AMino-5-(forMaMidoMethyl)-2-MethylpyriMidine
• Synonyms: 4-AMino-5-(forMaMidoMethyl)-2-MethylpyriMidine;2-Methyl-4-amino-5-(formylaminomethyl)pyrimidine
• CAS NO: 1886-34-6
• Molecular Formula: C₇H₁₀N₄O
• Molecular Weight: 166.1805
• Product Categories: Amines, Aromatics, Heterocycles, Metabolites & Impurities, Pharmaceuticals, Intermediates & Fine Chemicals, Sulfur & Selenium Compounds
• Mol File: 1886-34-6.mol
• Article Data: 8

Chemical Properties

• Melting Point: 227-228 °C
• Boiling Point: 452°C at 760 mmHg
• Flash Point: 227.2°C
• Appearance: /
• Density: 1.245g/cm³
• Vapor Pressure: 2.32E-08mmHg at 25°C
• Refractive Index: 1.586
• Storage Temp.: Amber Vial, -20°C Freezer, Under inert atmosphere
• Solubility: DMSO (Slightly), Methanol (Very Slightly, Sonicated)
• PKA: 14.77±0.23(Predicted)
• Stability: Air Sensitive, Light Sensitive
• CAS DataBase Reference: 4-AMino-5-(forMaMidoMethyl)-2-MethylpyriMidine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-AMino-5-(forMaMidoMethyl)-2-MethylpyriMidine(1886-34-6)
• EPA Substance Registry System: 4-AMino-5-(forMaMidoMethyl)-2-MethylpyriMidine(1886-34-6)

Safety Data

• Hazardous Substances Data: 1886-34-6(Hazardous Substances Data)

Usage

Uses

4-Amino-5-(formamidomethyl)-2-methylpyrimidine is a metabolite of thiamine (T344185), a essential nutrient required for carbohydrate metabolism; also involved in nerve function.

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

• 119206-80-3 α-phenyl-aminomethylene-β-formylaminopropionitrile 
• 143-37-3 acetamidine 
• 75-05-8 acetonitrile 
• 106030-08-4 α-formyl-β-formylaminopropionitrile sodium salt 
• 124-42-5 acetamidine hydrochloride 
• 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 
• 14273-76-8 ethyl 2-(4-chloro-2-methylpyrimidin-5-yl)acetate 
• 220895-93-2 (4-amino-2-methyl-pyrimidin-5-yl)-acetic acid ethyl ester 
• 412277-96-4 4-amino-2-hydroxymethyl-pyrimidine-5-carbonitrile 
• 42981-14-6 2-(4-amino-2-methylpyrimidin-5-yl)acetamide 
• 698-29-3 2-methyl-4-amino-5-cyanopyrimidine 
• 98335-69-4 (4-amino-2-methyl-pyrimidin-5-yl)-acetic acid hydrazide 
• 31375-20-9 4-Amino-2-methyl-5-thioformamidomethylpyrimidin 

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 
• 70732-86-4 thiamine hydrochloride 
• 141-53-7 sodium formate 
• 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 articles and documents

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.

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.

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.