6-Bromo-2-chloro-8-cyclopentyl-5-methylpyrido-[2,3-d]pyrimidin-7(8H)-one (CAS 1016636-76-2): A Comprehensive Product Introduction

General Overview

6-Bromo-2-chloro-8-cyclopentyl-5-methylpyrido-[2,3-d]pyrimidin-7(8H)-one, with the CAS number 1016636-76-2, is a highly significant chemical compound in the field of organic chemistry. This compound has drawn considerable attention due to its unique chemical structure and potential applications in various industries. Its complex molecular structure consists of a pyrido[2,3-d]pyrimidin-7(8H)-one core, substituted with bromo, chloro, cyclopentyl, and methyl groups at specific positions. These substituents play a crucial role in determining its physical and chemical properties, as well as its reactivity and biological activity.

Physical and Chemical Properties

The physical properties of 6-Bromo-2-chloro-8-cyclopentyl-5-methylpyrido-[2,3-d]pyrimidin-7(8H)-one are important for understanding its behavior and handling. It typically exists as a solid at room temperature, with a specific melting point that can be determined through precise experimental methods. The compound’s solubility in different solvents is also a key characteristic. It may have limited solubility in water but show better solubility in organic solvents such as ethanol, acetone, and dimethyl sulfoxide (DMSO). This solubility profile is essential for its use in various chemical reactions and biological assays.

Chemically, the bromo and chloro substituents on the molecule can participate in a variety of reactions. The bromine atom, for example, can undergo nucleophilic substitution reactions, allowing for the introduction of other functional groups at that position. The chlorine atom also has similar reactivity, providing opportunities for further chemical modifications. The cyclopentyl and methyl groups contribute to the overall hydrophobicity of the compound, which can influence its interactions with biological membranes and proteins.

Applications

Pharmaceutical Industry

In the pharmaceutical industry, 6-Bromo-2-chloro-8-cyclopentyl-5-methylpyrido-[2,3-d]pyrimidin-7(8H)-one has shown great potential as a lead compound for drug discovery. Its unique structure allows it to interact with specific biological targets, such as enzymes and receptors. For example, it may act as an inhibitor of certain kinases, which are important proteins involved in cell signaling pathways. By inhibiting these kinases, the compound could potentially be used to treat diseases such as cancer, where abnormal kinase activity is often observed.

Preclinical studies have demonstrated that derivatives of this compound can have potent anti – tumor activity in cell lines and animal models. These derivatives may be designed to have improved pharmacokinetic properties, such as better absorption, distribution, metabolism, and excretion (ADME) characteristics. In addition, the compound may also have applications in the treatment of inflammatory diseases, as it could modulate the immune response by interacting with relevant signaling pathways.

Agrochemical Industry

In the agrochemical industry, 6-Bromo-2-chloro-8-cyclopentyl-5-methylpyrido-[2,3-d]pyrimidin-7(8H)-one could be used as a starting material for the synthesis of novel pesticides. Its chemical structure can be modified to target specific pests, such as insects, fungi, or weeds. For example, by introducing appropriate functional groups, the compound could be made to act as an insecticide by interfering with the insect’s nervous system or metabolic processes. Similarly, it could be developed into a fungicide by inhibiting the growth and reproduction of fungi.

Moreover, the compound’s stability and solubility properties make it suitable for formulation into various agrochemical products, such as emulsifiable concentrates, wettable powders, or granules. These formulations can be easily applied to crops using different methods, such as spraying or dusting, to provide effective pest control.

Material Science

In material science, 6-Bromo-2-chloro-8-cyclopentyl-5-methylpyrido-[2,3-d]pyrimidin-7(8H)-one can be used as a building block for the synthesis of new functional materials. Its reactive groups allow it to be incorporated into polymers or other macromolecules, imparting specific properties to the resulting materials. For example, it could be used to synthesize conductive polymers, which have applications in electronics, such as in the development of organic light – emitting diodes (OLEDs) or solar cells.

The compound’s unique structure can also contribute to the mechanical and thermal properties of the materials. By carefully controlling the synthesis conditions, materials with tailored properties, such as high strength, flexibility, or thermal stability, can be obtained. This makes it a valuable component in the development of advanced materials for various industries.

Synthesis and Preparation Methods

General Synthetic Strategies

The synthesis of 6-Bromo-2-chloro-8-cyclopentyl-5-methylpyrido-[2,3-d]pyrimidin-7(8H)-one typically involves a multi – step process. One common approach starts with the construction of the pyrido[2,3-d]pyrimidin-7(8H)-one core. This can be achieved through a series of condensation and cyclization reactions. For example, appropriate pyridine and pyrimidine derivatives can be reacted under specific conditions to form the basic ring structure.

Once the core structure is formed, the bromo, chloro, cyclopentyl, and methyl groups are introduced through subsequent substitution reactions. The bromination and chlorination steps usually involve the use of specific brominating and chlorinating agents, such as N – bromosuccinimide (NBS) and thionyl chloride (SOCl₂), respectively. The introduction of the cyclopentyl and methyl groups may require the use of appropriate alkylating agents and catalysts.

Optimized Synthesis Routes

To improve the yield and purity of 6-Bromo-2-chloro-8-cyclopentyl-5-methylpyrido-[2,3-d]pyrimidin-7(8H)-one, several optimized synthesis routes have been developed. These routes often involve the use of mild reaction conditions, such as low temperatures and environmentally friendly solvents. For example, microwave – assisted synthesis has been explored as a more efficient method, which can significantly reduce the reaction time and increase the yield.

In addition, the use of chiral catalysts in the synthesis can be employed to obtain enantiomerically pure products, which may be important for their biological activity. By carefully selecting the reaction conditions and reagents, a high – quality product can be obtained with good reproducibility.

Safety and Handling

As with any chemical compound, proper safety precautions should be taken when handling 6-Bromo-2-chloro-8-cyclopentyl-5-methylpyrido-[2,3-d]pyrimidin-7(8H)-one. It is recommended to wear appropriate personal protective equipment, such as gloves, goggles, and a lab coat, to avoid direct contact with the compound. In case of skin or eye contact, immediate washing with plenty of water is required, and medical attention should be sought if necessary.

The compound should be stored in a cool, dry place, away from sources of heat and ignition. It should also be kept in a well – ventilated area to prevent the accumulation of vapors. When disposing of the compound, it should be done in accordance with local environmental regulations.

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References

• Reference 1: General Overview of Pyrido[2,3-d]pyrimidine Derivatives
• Reference 2: Synthesis and Biological Activity of Bromo – Chloro Substituted Heterocycles
• Reference 3: Applications of Organic Compounds in the Pharmaceutical Industry

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