2-Amino-4-chloro-6-methoxypyrimidine
[CAS# 5734-64-5]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Methoxypyrimidine
• Name: 2-Amino-4-chloro-6-methoxypyrimidine
• Synonyms: 4-Chloro-6-methoxy-2-pyrimidinamine
• Molecular Formula: C₅H₆ClN₃O
• Molecular Weight: 159.57
• CAS Registry Number: 5734-64-5
• EC Number: 611-506-1
• SMILES: COC1=CC(=NC(=N1)N)Cl

Properties

• Density: 1.4±0.1 g/cm³, Calc.^*
• Melting point: 168-171 °C
• Index of Refraction: 1.585, Calc.^*
• Boiling Point: 349.4±45.0 °C (760 mmHg), Calc.^*
• Flash Point: 165.1±28.7 °C, 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.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovery and Applications

2-Amino-4-chloro-6-methoxypyrimidine, with the chemical formula C6H7ClN4O, is a pyrimidine derivative that has garnered attention due to its diverse applications in pharmaceutical and agricultural chemistry. The discovery of this compound dates back to the mid-20th century, during an era of significant advancements in the synthesis and application of heterocyclic compounds. Researchers were exploring various pyrimidine derivatives for their potential biological activities, leading to the identification of 2-amino-4-chloro-6-methoxypyrimidine as a compound of interest.

The synthesis of 2-amino-4-chloro-6-methoxypyrimidine typically involves the chlorination and methoxylation of pyrimidine derivatives. Various synthetic routes have been developed, allowing for efficient production and modification of this compound. The introduction of the amino and methoxy groups on the pyrimidine ring enhances its reactivity and biological activity, making it a valuable intermediate in the development of pharmaceuticals.

One of the primary applications of 2-amino-4-chloro-6-methoxypyrimidine is in the pharmaceutical industry, particularly in the synthesis of antiviral and antimicrobial agents. This compound serves as a crucial building block in the development of nucleoside analogs, which are essential in treating viral infections such as hepatitis and HIV. Its structural similarity to naturally occurring nucleotides allows it to interfere with viral replication, providing therapeutic benefits.

Moreover, 2-amino-4-chloro-6-methoxypyrimidine is also employed in the agricultural sector as a herbicide and plant growth regulator. The compound exhibits selective herbicidal activity against certain weed species, making it useful in the formulation of herbicidal products. By inhibiting specific biochemical pathways in target plants, it contributes to effective weed management strategies, enhancing crop yield and quality.

The compound's versatility extends beyond agriculture and pharmaceuticals; it also finds applications in the development of agrochemicals and other specialty chemicals. Researchers continue to explore modifications of the pyrimidine structure to optimize its activity and efficacy in various applications, contributing to ongoing advancements in medicinal chemistry and agricultural sciences.

Despite its beneficial applications, the environmental impact of using chlorinated compounds like 2-amino-4-chloro-6-methoxypyrimidine in agriculture must be carefully assessed. Regulatory frameworks are in place to evaluate the safety and environmental effects of such compounds, ensuring responsible usage that mitigates potential risks to ecosystems.

In conclusion, 2-amino-4-chloro-6-methoxypyrimidine represents a significant advancement in the field of heterocyclic chemistry, with valuable applications in pharmaceuticals and agriculture. Its discovery has paved the way for further research into pyrimidine derivatives, highlighting its importance as a building block in the development of therapeutic agents and crop protection products.

References

2012. 4-Chloro-6-meth-oxy-pyrimidin-2-amine. Acta crystallographica. Section E, Structure reports online, 68(12).
DOI: 10.1107/s160053681204528x