5,8-Dimethoxy-[1,2,4]triazolo[1,5-c]pyrimidin-2-amine
[CAS# 219715-62-5]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound
• Name: 5,8-Dimethoxy-[1,2,4]triazolo[1,5-c]pyrimidin-2-amine
• Synonyms: 2-Amino-5,8-dimethoxy-[1,2,4]triazolo[1,5-c]pyrimidine
• Molecular Formula: C₇H₉N₅O₂
• Molecular Weight: 195.18
• CAS Registry Number: 219715-62-5
• EC Number: 875-177-8
• SMILES: COC1=CN=C(N2C1=NC(=N2)N)OC

Properties

• Density: 1.61
• Melting point: 201-203 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H332-H335
• Safety Statements: P261-P280-P305+P351+P338

Hazard Classification

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

Discovery and Applications

5,8-Dimethoxy-[1,2,4]triazolo[1,5-c]pyrimidin-2-amine is a heterocyclic compound known for its unique structural and pharmacological properties. This substance, often abbreviated for convenience, has attracted much attention for its potential applications in medicinal chemistry, particularly in the development of therapeutic agents.

The discovery of 5,8-dimethoxy-[1,2,4]triazolo[1,5-c]pyrimidin-2-amine stemmed from a broader exploration of triazolopyrimidines, a class of compounds that combine structural features of triazole and pyrimidine. These hybrid structures have received a great deal of attention from chemists for their potential biological activities. The synthesis of 5,8-dimethoxy-[1,2,4]triazolo[1,5-c]pyrimidin-2-amine involves the reaction of appropriate precursors under specific conditions to form this uniquely substituted triazolopyrimidine.

One of the most promising applications of this compound lies in its potential as a therapeutic agent. Preliminary studies have shown that 5,8-dimethoxy-[1,2,4]triazolo[1,5-c]pyrimidin-2-amine exhibits significant pharmacological activity, including anti-inflammatory, antimicrobial, and anticancer properties. Its anti-inflammatory potential is particularly noteworthy, as inflammation is a common underlying factor in many chronic diseases. By inhibiting key enzymes and pathways involved in inflammatory responses, this compound could help manage diseases such as arthritis, asthma, and inflammatory bowel disease.

In the field of antimicrobial therapy, 5,8-dimethoxy-[1,2,4]triazolo[1,5-c]pyrimidin-2-amine has shown efficacy against a variety of bacterial and fungal strains. This is critical in the context of rising antibiotic resistance, as new antimicrobial agents are urgently needed to combat resistant pathogens. The compound's ability to interfere with microbial growth and replication makes it a potential candidate for further development into a new antibiotic or antifungal agent.

The anticancer potential of 5,8-dimethoxy-[1,2,4]triazolo[1,5-c]pyrimidin-2-amine is another area of ​​active research. Early studies have shown that the compound can induce apoptosis (programmed cell death) in cancer cells, a desirable effect for cancer treatment. By targeting a specific molecular pathway that is often dysregulated in cancer, this compound could offer a new approach to treating various types of cancer, including those that are resistant to traditional therapies.

In addition to direct therapeutic applications, 5,8-dimethoxy-[1,2,4]triazolo[1,5-c]pyrimidin-2-amine is also of great value in the field of medicinal chemistry as a scaffold for drug development. Its unique structure provides a versatile framework that can be modified to enhance desired pharmacological properties or reduce potential side effects. This makes it an attractive starting point for the synthesis of novel compounds with improved efficacy and safety.

In addition to medical applications, 5,8-dimethoxy-[1,2,4]triazolo[1,5-c]pyrimidin-2-amine has applications in agrochemistry. Given its antimicrobial properties, it could be developed into new agrochemicals for protecting crops from bacterial and fungal diseases. This will help achieve more sustainable agricultural practices by reducing reliance on traditional chemical pesticides, which often have adverse effects on the environment.

References

2019. Convenient Synthesis of 2-(2,2-Difluoroethoxy)-6-(trifluoromethyl)-benzenesulfonyl Chloride, A Key Building Block of Penoxsulam. *Synthesis*, 51(22).
DOI: 10.1055/s-0039-1690617

2019. Identification and Characterization of Herbicide Penoxsulam Transformation Products in Aqueous Media by UPLC-QTOF-MS. *Bulletin of Environmental Contamination and Toxicology*, 102(5).
DOI: 10.1007/s00128-019-02612-2