4,6-Dichloro-2-methylpyrimidine
[CAS# 1780-26-3]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Methyl pyrimidine
• Name: 4,6-Dichloro-2-methylpyrimidine
• Molecular Formula: C₅H₄Cl₂N₂
• Molecular Weight: 163.00
• CAS Registry Number: 1780-26-3
• EC Number: 605-815-0
• SMILES: CC1=NC(=CC(=N1)Cl)Cl

Properties

• Density: 1.4±0.1 g/cm³, Calc.^*
• Melting point: 41.5-45.5 °C (expl.)
• Index of Refraction: 1.551, Calc.^*
• Boiling Point: 210.8±20.0 °C (760 mmHg), Calc.^*
• Flash Point: 101.1±7.4 °C, Calc.^*, 97 °C (expl.)

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

Safety Data

• Hazard Symbols: GHS05;GHS07;GHS09 Danger
• Risk Statements: H302-H314-H317-H411
• Safety Statements: P260-P261-P264-P270-P272-P273-P280-P301+P317-P301+P330+P331-P302+P352-P302+P361+P354-P304+P340-P305+P354+P338-P316-P321-P330-P333+P317-P362+P364-P363-P391-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Acute toxicity	Acute Tox.	4	H302
Skin sensitization	Skin Sens.	1	H317
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin corrosion	Skin Corr.	1B	H314
Serious eye damage	Eye Dam.	1	H318

• Transport Information: UN 3261

Discovery and Applications

4,6-Dichloro-2-methylpyrimidine is an important organic compound that contains both chlorine atoms and a methyl group attached to a pyrimidine ring. Pyrimidine derivatives, such as 4,6-dichloro-2-methylpyrimidine, have a broad range of applications in the fields of medicinal chemistry, agrochemicals, and material science due to their versatile chemical properties. The compound is of particular interest because of its reactivity and the biological activities associated with pyrimidine derivatives.

The discovery of 4,6-dichloro-2-methylpyrimidine is part of the ongoing exploration of pyrimidine chemistry, which began in the early 20th century. Pyrimidines are aromatic heterocyclic compounds composed of a six-membered ring containing nitrogen atoms at positions 1, 3, and 5. Various derivatives of pyrimidine have been synthesized, and their diverse biological activities have spurred interest in their applications. 4,6-Dichloro-2-methylpyrimidine is synthesized through a halogenation reaction of 2-methylpyrimidine, where chlorine atoms are introduced at the 4 and 6 positions of the pyrimidine ring.

4,6-Dichloro-2-methylpyrimidine has found applications primarily in the synthesis of pharmaceutical compounds, especially in the development of antiviral and anticancer drugs. The chlorine atoms at the 4 and 6 positions of the pyrimidine ring enhance its ability to interact with various biological targets. For example, this compound is used as a building block in the synthesis of more complex molecules that can inhibit the activity of enzymes involved in disease processes. In particular, pyrimidine derivatives are well-known for their ability to inhibit DNA and RNA synthesis, making them valuable for the treatment of cancer and viral infections.

One of the key therapeutic areas where 4,6-dichloro-2-methylpyrimidine has been investigated is in antiviral drug development. Pyrimidine derivatives, including 4,6-dichloro-2-methylpyrimidine, have been found to interfere with viral replication by inhibiting viral polymerases. This action makes them potential candidates for treating infections such as HIV, hepatitis, and herpes simplex virus. The ability of 4,6-dichloro-2-methylpyrimidine to disrupt viral processes is highly beneficial for the design of novel antiviral agents that target specific stages of the viral life cycle.

In addition to its pharmaceutical applications, 4,6-dichloro-2-methylpyrimidine is also useful in the field of agrochemicals. It is utilized in the synthesis of herbicides and pesticides that target specific plant enzymes or processes. The presence of chlorine atoms in the compound enhances its stability and potency as an herbicide, making it effective in controlling the growth of unwanted vegetation in agricultural settings. By modifying the methyl group or introducing additional functional groups, it is possible to tailor the compound's properties for specific applications in crop protection.

Furthermore, the chemical reactivity of 4,6-dichloro-2-methylpyrimidine makes it a useful intermediate in organic synthesis. It serves as a key precursor for the synthesis of a variety of pyrimidine-based molecules, which have applications in materials science, including the development of organic semiconductors and light-emitting diodes (LEDs). Pyrimidine derivatives are also being explored for their potential use in electronic devices due to their ability to form conductive films and semiconducting polymers.

Despite its promising applications, 4,6-dichloro-2-methylpyrimidine's potential in drug development and other fields requires continued research. One of the challenges in its application is the optimization of its pharmacokinetic and pharmacodynamic properties to ensure its efficacy and safety. Researchers continue to explore ways to improve the bioavailability and selectivity of pyrimidine-based compounds, which may lead to the development of more effective drugs and agrochemicals.

In conclusion, 4,6-dichloro-2-methylpyrimidine is a versatile chemical compound with significant applications in the pharmaceutical and agrochemical industries. Its reactivity, biological activity, and utility as a building block for more complex molecules make it a valuable tool in drug discovery, particularly for antiviral and anticancer therapies. As research progresses, this compound is expected to contribute to the development of new treatments for various diseases and to the advancement of technologies in the fields of agriculture and materials science.

References

2023. Chrysin based pyrimidine-piperazine hybrids: design, synthesis, in vitro antimicrobial and in silico E. coli topoisomerase II DNA gyrase efficacy. Molecular Diversity.
DOI: 10.1007/s11030-023-10663-1

2020. Substitution of Halogens by Aromatic Amines. Science of Synthesis.
URL: https://science-of-synthesis.thieme.com/app/text/?id=SD-116-01364

2013. Biological evaluation of 2-methylpyrimidine derivatives as active pan Bcr-Abl inhibitors. Science China Chemistry.
DOI: 10.1007/s11426-013-5011-9