2-Amino-4,6-dimethoxypyrimidine
[CAS# 36315-01-2]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Methoxypyrimidine
• Name: 2-Amino-4,6-dimethoxypyrimidine
• Synonyms: 4,6-Dimethoxypyrimidin-2-amine
• Molecular Formula: C₆H₉N₃O₂
• Molecular Weight: 155.16
• CAS Registry Number: 36315-01-2
• EC Number: 252-969-6
• SMILES: COC1=CC(=NC(=N1)N)OC

Properties

• Melting point: 94-96 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302+H312+H332-H302-H312-H315-H319-H332-H335
• Safety Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P317-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	4	H332
Eye irritation	Eye Irrit.	2A	H319
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410

Discovery and Applications

2-Amino-4,6-dimethoxypyrimidine is a pyrimidine derivative that has garnered attention for its significant applications in pharmaceuticals and agricultural chemistry. The compound features an amino group at the 2-position and methoxy groups at the 4 and 6 positions of the pyrimidine ring, contributing to its unique chemical properties and biological activities. The discovery of this compound can be traced back to research in the mid-20th century aimed at exploring various nitrogen-containing heterocycles, which are known for their diverse biological activities.

Synthesis of 2-amino-4,6-dimethoxypyrimidine typically involves the alkylation of pyrimidine derivatives or the use of readily available precursors such as uracil. The introduction of the amino and methoxy substituents can be achieved through various organic transformations, including methylation and amination reactions. This synthetic flexibility has facilitated the exploration of the compound and its derivatives, leading to an understanding of its reactivity and potential uses.

In pharmaceutical research, 2-amino-4,6-dimethoxypyrimidine has been investigated for its potential as an antitumor agent. Studies have shown that derivatives of this compound exhibit cytotoxic effects against various cancer cell lines, suggesting a role in the development of novel chemotherapeutic agents. Its ability to interfere with specific cellular pathways makes it a target for further exploration in drug development, particularly in the design of pyrimidine-based anticancer drugs.

Apart from its antitumor potential, 2-amino-4,6-dimethoxypyrimidine has also been explored for its antibacterial properties. Research indicates that certain derivatives possess significant activity against a range of bacterial strains, including both Gram-positive and Gram-negative bacteria. This has led to interest in the compound's potential applications in developing new antibiotics, addressing the growing concern of antibiotic resistance.

In agriculture, 2-amino-4,6-dimethoxypyrimidine has been examined for its herbicidal properties. Its structural features enable it to act as a growth regulator or herbicide, providing an avenue for the development of new agrochemicals that can enhance crop yield and management. The compound's ability to selectively target specific pathways in plants can lead to effective weed management strategies while minimizing harm to crops.

In summary, 2-amino-4,6-dimethoxypyrimidine is a versatile compound with significant implications in pharmaceuticals and agriculture. Its discovery has opened avenues for the development of novel therapeutic agents and agrochemicals. As research continues to unveil the potential of this compound, it is expected to play a crucial role in addressing health and agricultural challenges.

References

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2023. Exploring Potential Coformer Screening Techniques Based on Experimental and Virtual Strategies in the Manufacturing of Pharmaceutical Cocrystal of Efavirenz. Journal of Pharmaceutical Innovation, 18(2).
DOI: 10.1007/s12247-022-09704-3