2-Amino-5,7-dimethoxy-1,2,4-triazolo[1,5-a]pyrimidine
[CAS# 13223-43-3]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound
• Name: 2-Amino-5,7-dimethoxy-1,2,4-triazolo[1,5-a]pyrimidine
• Synonyms: 5,7-dimethoxy-[1,2,4]triazolo[1,5-a]pyrimidin-2-amine
• Molecular Formula: C₇H₉N₅O₂
• Molecular Weight: 195.18
• CAS Registry Number: 13223-43-3
• EC Number: 603-562-0
• SMILES: COC1=CC(=NC2=NC(=NN12)N)OC

Properties

• Density: 1.6±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.706, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302
• Safety Statements: P264-P270-P301+P317-P330-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Eye irritation	Eye Irrit.	2A	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315

Discovery and Applications

2-Amino-5,7-dimethoxy-1,2,4-triazolo[1,5-a]pyrimidine is a heterocyclic compound recognized for its unique structural properties and potential applications in pharmaceuticals and agriculture. The compound belongs to the class of triazolopyrimidines, characterized by the presence of both triazole and pyrimidine rings in its structure. The discovery of this compound is rooted in the ongoing exploration of nitrogen-containing heterocycles, which have garnered significant interest due to their biological activities and utility in drug development.

The synthesis of 2-amino-5,7-dimethoxy-1,2,4-triazolo[1,5-a]pyrimidine typically involves the reaction of suitable precursors under specific conditions to facilitate the formation of the triazole and pyrimidine moieties. Early studies focused on the synthesis of various substituted triazolopyrimidines, highlighting their diverse biological activities, including antifungal, antibacterial, and antitumor properties. These investigations paved the way for the development of 2-amino-5,7-dimethoxy-1,2,4-triazolo[1,5-a]pyrimidine as a compound of interest in medicinal chemistry.

One of the primary applications of 2-amino-5,7-dimethoxy-1,2,4-triazolo[1,5-a]pyrimidine lies in its potential as a pharmaceutical agent. Research has demonstrated that compounds within this class can exhibit significant biological activity against various diseases, including infections and cancers. The presence of amino and methoxy groups in its structure is believed to enhance the compound's efficacy and specificity, making it a candidate for further investigation in drug development.

In addition to its pharmaceutical applications, 2-amino-5,7-dimethoxy-1,2,4-triazolo[1,5-a]pyrimidine has been explored for its potential use in agricultural chemistry. The compound's ability to modulate biological pathways can lead to the development of novel agrochemicals aimed at enhancing crop protection and yield. Its application in this field aligns with the growing demand for sustainable agricultural practices and the need for effective, environmentally friendly pest management solutions.

Furthermore, the compound's unique structure lends itself to further modifications, allowing researchers to synthesize analogs with improved properties. This adaptability is crucial in medicinal chemistry, where the optimization of compounds can lead to enhanced potency and reduced side effects.

In conclusion, 2-amino-5,7-dimethoxy-1,2,4-triazolo[1,5-a]pyrimidine is a compound of considerable interest due to its unique chemical structure and potential applications in pharmaceuticals and agriculture. Its discovery has opened avenues for further research, aiming to exploit its biological activities and develop effective therapeutic and agrochemical agents.

References

2007. A new approach to synthesis of 2-sulfonylamino-1,2,4-triazolo[1,5-a]pyrimidines. Russian Journal of Applied Chemistry, 80(10).
DOI: 10.1134/s1070427207100175