Ethyl 2-chloro-4-(cyclopropylamino)pyrimidine-5-carboxylate
[CAS# 1192711-36-6]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: Ethyl 2-chloro-4-(cyclopropylamino)pyrimidine-5-carboxylate
• Molecular Formula: C₁₀H₁₂ClN₃O₂
• Molecular Weight: 241.68
• CAS Registry Number: 1192711-36-6
• SMILES: CCOC(=O)C1=CN=C(N=C1NC2CC2)Cl

Properties

• Density: 1.4±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.626, Calc.^*
• Boiling Point: 411.2±25.0 ºC (760 mmHg), Calc.^*
• Flash Point: 202.5±23.2 ºC, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H335
• Precautionary Statements: P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Discovory and Applicatios

Ethyl 2-chloro-4-(cyclopropylamino)pyrimidine-5-carboxylate is a chemical compound that has attracted attention due to its unique structure and potential applications in medicinal chemistry. This molecule is characterized by the presence of a pyrimidine ring, which is substituted at the 2-position with a chloro group, at the 4-position with a cyclopropylamino group, and at the 5-position with an ethyl ester group. The distinct arrangement of functional groups gives this compound its unique properties, which can be leveraged in various chemical and pharmaceutical applications.

The discovery of ethyl 2-chloro-4-(cyclopropylamino)pyrimidine-5-carboxylate is part of an ongoing effort to develop novel pyrimidine derivatives with diverse biological activities. Pyrimidine is a heterocyclic compound that serves as the backbone for many biologically active molecules. Substituting the pyrimidine ring with different functional groups, such as chloro and cyclopropylamino, can significantly alter the compound's reactivity, solubility, and ability to interact with biological targets. The chloro group, in particular, can influence the compound’s electrophilicity, while the cyclopropylamino group can introduce strain and unique steric effects that may enhance its bioactivity.

Ethyl 2-chloro-4-(cyclopropylamino)pyrimidine-5-carboxylate holds promise for application in drug discovery, particularly in the development of agents targeting various enzymatic pathways. Pyrimidine derivatives are known for their activity as kinase inhibitors, which makes them valuable in the treatment of diseases such as cancer and autoimmune disorders. The incorporation of a cyclopropylamino group into the pyrimidine structure may provide the compound with unique binding properties, potentially allowing it to bind to specific targets with high selectivity. This selectivity is critical in drug design, as it minimizes side effects and maximizes therapeutic efficacy.

Additionally, the ethyl ester group at the 5-position of the pyrimidine ring can enhance the compound's lipophilicity, which could improve its ability to cross biological membranes and reach intracellular targets. This property is often desirable in drug design, especially for small molecule inhibitors that need to penetrate cells to exert their effects. The ester group could also be hydrolyzed in vivo to release the active carboxylate form, allowing for a sustained release of the bioactive species.

One potential therapeutic application of ethyl 2-chloro-4-(cyclopropylamino)pyrimidine-5-carboxylate could be in the treatment of cancer. Pyrimidine-based compounds, including those with structural motifs similar to this molecule, have been investigated for their ability to inhibit various kinases involved in tumor growth and metastasis. The selective inhibition of kinases that regulate cell proliferation and survival could offer a strategy for combating cancerous cells without affecting normal, healthy tissues. This type of targeted therapy is a significant area of research in oncology, where there is an ongoing need for more effective and less toxic treatments.

Beyond cancer, this compound may also have potential in the treatment of neurological disorders, particularly those involving neurotransmitter imbalances. The cyclopropylamino group could allow the compound to interact with receptors in the central nervous system, providing a possible avenue for the development of drugs aimed at modulating neurotransmitter activity. For instance, compounds with similar structures have been explored for their potential to act as selective inhibitors of enzymes involved in neurotransmitter degradation or uptake.

Moreover, the synthetic flexibility of ethyl 2-chloro-4-(cyclopropylamino)pyrimidine-5-carboxylate means that it could serve as an intermediate in the preparation of other more complex molecules. The ability to modify the pyrimidine ring and its substituents opens up possibilities for designing a broad range of derivatives with tailored pharmacological properties. This makes it a valuable scaffold in medicinal chemistry and pharmaceutical development.

In conclusion, ethyl 2-chloro-4-(cyclopropylamino)pyrimidine-5-carboxylate is a versatile and promising compound with potential applications in drug discovery and development. Its unique structure, featuring both a chloro group and a cyclopropylamino group, makes it an attractive candidate for targeting a range of diseases, particularly cancer and neurological disorders. As research into its properties and applications progresses, this compound could play a significant role in the development of new therapeutic agents.