3289-50-7

Basic information

• Product Name: 4-Amino-2,6-dimethoxypyrimidine
• Synonyms: 2,6-dimethoxy-4-pyrimidinamin;4-AMINO-2,6-DIMETHOXYPYRIMIDINE;2,4-DIMETHOXY-6-AMINOPYRIMIDINE;2,6-DIMETHOXYPYRIMIDIN-4-AMINE;2,6-Dimethoxy-4-aminopyrimidine;4-Amino-4,6-dimethoxypyrimidine;4-Amino-2,6-dimethoxy;4-amino-2,6-dlmethoxypyrimidine
• CAS NO: 3289-50-7
• Molecular Formula: C₆H₉N₃O₂
• Molecular Weight: 155.15
• EINECS: 221-946-2
• Product Categories: Pyrimidine;(intermediate of sulphadimethoxine);Building Blocks;Heterocyclic Building Blocks;Pyrimidines;Heterocycle-Pyrimidine series
• Mol File: 3289-50-7.mol
• Article Data: 10

Chemical Properties

• Melting Point: 149-152 °C(lit.)
• Boiling Point: 340.1 ºC at 760 mmHg
• Flash Point: 159.5 ºC
• Appearance: White/Crystalline
• Density: 1.229 g/cm³
• Vapor Pressure: 8.79E-05mmHg at 25°C
• Refractive Index: 1.547
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility: methanol: soluble25mg/mL, clear, colorless to yellow
• PKA: 3.35±0.10(Predicted)
• CAS DataBase Reference: 4-Amino-2,6-dimethoxypyrimidine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Amino-2,6-dimethoxypyrimidine(3289-50-7)
• EPA Substance Registry System: 4-Amino-2,6-dimethoxypyrimidine(3289-50-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• TSCA: Yes
• HazardClass: IRRITANT
• Hazardous Substances Data: 3289-50-7(Hazardous Substances Data)

Usage

Description

4-Amino-2,6-dimethoxypyrimidine is a methoxy-substituted 4-aminopyrimidine compound with potential polychlorination. It is characterized by its molecular structure, which features N-H.O and N-H.N hydrogen bonds, forming sheets with centrosymmetric rings. 4-Amino-2,6-dimethoxypyrimidine has been studied for its photocatalytic degradation on TiO2 and its mass spectra.

Uses

Used in Pharmaceutical Industry:
4-Amino-2,6-dimethoxypyrimidine is used as an impurity in the production of Sulfadimethoxine (S699060), an antibacterial agent. It is recognized as Sulfadimethoxine EP Impurity A and is a contaminant of concern due to its potential environmental and health impacts.
Used in Environmental Science:
4-Amino-2,6-dimethoxypyrimidine is used as a subject of study in environmental science, particularly in the context of photocatalytic degradation on TiO2. This research is important for understanding the compound's behavior in the environment and its potential impact on ecosystems.
Used in Analytical Chemistry:
The mass spectra of 4-amino-2,6-dimethoxypyrimidine have been studied, making it a subject of interest in analytical chemistry. This information is valuable for the identification and quantification of the compound in various samples, such as environmental or pharmaceutical products.

InChI:InChI=1/C6H9N3O2/c1-10-5-3-4(7)8-6(9-5)11-2/h3H,1-2H3,(H2,7,8,9)

Upstream product

• 6320-15-6 6-chloro-2,4-dimethoxypyrimidine 
• 57-13-6 urea 
• 105-34-0 methyl 2-cyanoacetate 
• 74-88-4 methyl iodide 
• 67-56-1 methanol 
• 3289-66-5 2-chloro-4-amino-6-methoxypyrimidine 
• 10132-07-7 4-amino-2,6-dichloropyrimidine 
• 124-41-4 sodium methylate 
• 873-83-6 4-Amino-2,6-dihydroxypyrimidine 
• 616-38-6 carbonic acid dimethyl ester 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 555-25-9 4-p-acetamidobenzenesulfonamido-2,6-dimethoxypyrimidine 
• 141368-27-6 ethyl 5,7-dimethoxyimidazo<1,2-c>pyrimidine-2-carboxylate 
• 37063-70-0 N-(2,6-dimethoxy-pyrimidin-4-yl)-4-nitro-benzenesulfonamide 
• 73978-74-2 6-amino-2,4-dimethoxy-5-nitropyrimidine 
• 6584-20-9 4-amino-5-bromo-2,6-dimethoxypyrimidine 
• 90057-09-3 2,4-dimethoxy-7H-pyrrolo<2,3-d>pyrimidine 
• 148214-54-4 4-acetylamino-5-bromo-2,6-dimethoxypyrimidine 
• 133185-44-1 5,6-Diamino-2,4-dimethoxypyrimidine 
• 73978-85-5 2,4-Dimethoxy-7-oxo-7,8-dihydropteridin 
• 73978-86-6 2,4-Dimethoxy-6-methyl-7-oxo-7,8-dihydropteridin 
• 73978-83-3 2,4-Dimethoxy-7-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyloxy)pteridin 
• 73978-84-4 4-methoxy-2-oxo-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-7-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyloxy)-1,2-dihydropteridin 
• 73978-76-4 2,4-Dimethoxy-5-nitro-6-<(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)amino>pyrimidin 
• 73978-75-3 2,4-Dimethoxy-5-nitro-6-<(2,3,5-tri-O-benzoyl-α-D-ribofuranosyl)amino>pyrimidin 

Relevant articles and documents

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Synthesis method of 4-amino-2,6-dimethoxyl pyrimidine

The invention discloses a synthesis method of 4-amino-2,6-dimethoxyl pyrimidine, and belongs to the technical field of medical technologies. The synthesis method comprises following steps: (1) aminolysis reaction: adding 4,6-dichloropyrimdine-5-formic acid into ammonia liquor to carry out aminolysis reactions to obtain 4-amino-6-chloropyrimdine-5-formic acid; (2) chlorination reaction: dissolving4-amino-6-chloropyrimdine-5-formic acid prepared in the step (1) in a water solution of a diluted acid, then adding a chlorination reagent, and carrying out chlorination reactions to obtain 4-amino-2,6-chloropyrimdine-5-formic acid; (3) decarboxylation reaction: in a solvent, carrying out high temperature decarboxylation of 4-amino-2,6-chloropyrimdine-5-formic acid prepared in the step (2) to obtain 4-amino-2,6-chloropyrimdine; and (4) methoxylation reaction: adding 4-amino-2,6-chloropyrimdine prepared in the step (3) into a methoxylation reagent, and carrying out methoxylation reactions to obtain 4-amino-2,6-dimethoxyl pyrimidine. The synthesis method adopts a novel synthesis route, which will not generate a large amount of phosphorus containing wastewater. The provided method is green and environmentally friendly and generates prominent social benefits.

Preparation method of 4-amino-2, 6-dimethoxypyrimidine

The invention discloses a preparation method of 4-amino-2, 6-dimethoxypyrimidine in the technical field of chemical synthesis. The preparation method comprises: (1) an addition reaction: adding anhydrous methanol, a solvent and malononitrile into a container and feeding dry hydrogen chloride gas into the container for an addition reaction, (2) a condensation reaction: adding a deacidification agent into 1, 3-dimethoxypropanediamidine hydrochloride obtained in the step (1) and adding cyanamide into the mixture for a condensation reaction, (3) a cyclization reaction: adding a Lewis acid protecting agent into 3-amino-3-methoxy-N-cyano-2-propionamidine obtained in the step (2) and feeding dry hydrogen chloride gas into the mixture for a cyclization reaction, and (4) a methoxylation reaction: adding methanol and sodium hydroxide into a container, stirring and dissolving the mixture, and then adding the mixture into the 2-chloro-4-amino-6-methoxypyrimidine obtained in the step (3) for a methoxylation reaction. The preparation method is a novel method for synthesizing 4-amino-2, 6-dimethoxypyrimidine and greatly reduces the amount of discharged pollutants.