2-Chloro-4,6-dimethoxypyrimidine
[CAS# 13223-25-1]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Methoxypyrimidine
• Name: 2-Chloro-4,6-dimethoxypyrimidine
• Synonyms: pent-4-enoyl chloride
• Molecular Formula: C₆H₇ClN₂O₂
• Molecular Weight: 174.58
• CAS Registry Number: 13223-25-1
• EC Number: 603-561-5
• SMILES: COC1=CC(=NC(=N1)Cl)OC

Properties

• Melting point: 100-105 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H319
• Safety Statements: P264-P264+P265-P270-P280-P301+P317-P305+P351+P338-P330-P337+P317-P501

Hazard Classification

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

Discovery and Applications

2-Chloro-4,6-dimethoxypyrimidine, also known as DMP, was first synthesized in the mid-20th century as part of research efforts aimed at developing new pyrimidine derivatives with potential applications in pharmaceuticals and agrochemicals. The discovery of DMP involved the chlorination of 4,6-dimethoxypyrimidine, resulting in the substitution of a chlorine atom at the 2-position of the pyrimidine ring. This chemical modification enhanced the compound's reactivity and allowed for further functionalization, paving the way for its diverse applications in various fields.

2-Chloro-4,6-dimethoxypyrimidine serves as a valuable intermediate in the synthesis of pharmaceutical compounds, particularly those targeting the central nervous system (CNS) and infectious diseases. Its pyrimidine scaffold and functional groups make it suitable for the introduction of various substituents and modifications, enabling the creation of diverse pharmacologically active molecules.

In the field of agrochemicals, 2-Chloro-4,6-dimethoxypyrimidine is utilized as a key intermediate in the synthesis of herbicides, fungicides, and insecticides. Its chemical reactivity allows for the introduction of functional groups that confer herbicidal, fungicidal, or insecticidal properties to the final compound. By incorporating DMP-derived motifs into agrochemical formulations, researchers can develop effective crop protection products that target specific pests or pathogens while minimizing environmental impact.

Beyond its applications in pharmaceuticals and agrochemicals, 2-Chloro-4,6-dimethoxypyrimidine finds utility in organic synthesis as a versatile building block for the construction of complex molecules. Its ease of functionalization and compatibility with various synthetic methodologies make it a valuable tool .

2-Chloro-4,6-dimethoxypyrimidine serves as a versatile coupling partner in cross-coupling reactions, such as Suzuki-Miyaura, Stille, and Heck reactions. Its chloropyrimidine moiety enables selective coupling with various nucleophiles or electrophiles under mild reaction conditions, facilitating the synthesis of diverse organic compounds with high efficiency and yield.

In chemical biology, 2-Chloro-4,6-dimethoxypyrimidine is employed as a chemical probe for studying enzyme function, protein-ligand interactions, and cellular processes. Researchers utilize DMP derivatives as selective inhibitors or affinity probes to elucidate the biological roles of target proteins and pathways.

References

2011. Exchange of Halogen for Alkoxides. Science of Synthesis.
URL: https://science-of-synthesis.thieme.com/app/text/?id=SD-116-00372

2015. General synthesis of 4-aryloxy-6-methylpyrimidin-2-amines and their fragmentation under positive electrospray ionization. Russian Journal of Organic Chemistry, 51(10).
DOI: 10.1134/s1070428015100127

2014. Metal Catalyzed Cross-Coupling Reactions in the Decoration of Pyrimidine, Pyridazine, and Pyrazine. Synthesis and Modification of Heterocycles by Metal-Catalyzed Cross-coupling Reactions.
DOI: 10.1007/7081_2014_138