4,6-Dichloro-5-(2-methoxyphenoxy)-2,2'-bipyrimidine
[CAS# 150728-13-5]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound
• Name: 4,6-Dichloro-5-(2-methoxyphenoxy)-2,2'-bipyrimidine
• Synonyms: Bosentan Related Compound 1
• Molecular Formula: C₁₅H₁₀Cl₂N₄O₂
• Molecular Weight: 349.18
• CAS Registry Number: 150728-13-5
• EC Number: 604-750-5
• SMILES: COC1=CC=CC=C1OC2=C(N=C(N=C2Cl)C3=NC=CC=N3)Cl

Safety Data

• Hazard Symbols: GHS05;GHS07 Danger
• Hazard Statements: H314-H315-H317-H319-H335
• Precautionary Statements: P260-P261-P264-P264+P265-P271-P272-P280-P301+P330+P331-P302+P352-P302+P361+P354-P304+P340-P305+P351+P338-P305+P354+P338-P316-P319-P321-P332+P317-P333+P317-P337+P317-P362+P364-P363-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Skin sensitization	Skin Sens.	1	H317
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2A	H319
Skin corrosion	Skin Corr.	1B	H314

Discovory and Applicatios

4,6-Dichloro-5-(2-methoxyphenoxy)-2,2'-bipyrimidine is a bipyrimidine derivative with intriguing properties, combining a bipyrimidine scaffold with a methoxyphenoxy group and chlorine atoms at the 4 and 6 positions. The bipyrimidine core, known for its ability to interact with biological targets, particularly enzymes and receptors, makes this compound a valuable candidate in medicinal chemistry. The addition of chlorine atoms enhances the compound’s reactivity and binding affinity, while the 2-methoxyphenoxy group modulates its solubility and electronic characteristics.

This compound was discovered as part of a broader effort to develop kinase inhibitors and DNA-binding agents. Bipyrimidine derivatives have been studied for their ability to inhibit kinase activity, an important target in cancer treatment. The presence of chlorine atoms at the 4 and 6 positions of the bipyrimidine ring can increase the compound’s ability to bind to active sites in kinases, enhancing its inhibitory effects. The 2-methoxyphenoxy group contributes to the specificity of the compound, allowing it to interact selectively with particular kinases, potentially minimizing off-target effects.

One of the primary applications of 4,6-Dichloro-5-(2-methoxyphenoxy)-2,2'-bipyrimidine lies in the development of kinase inhibitors for cancer therapy. Kinases play a critical role in cellular signaling, and their dysregulation is linked to tumor growth and metastasis. By selectively inhibiting specific kinases, this compound has the potential to disrupt aberrant signaling pathways, slowing cancer progression. The bipyrimidine framework, known for its strong interaction with ATP-binding sites, enhances the compound’s efficacy as a kinase inhibitor.

Another area of interest for 4,6-Dichloro-5-(2-methoxyphenoxy)-2,2'-bipyrimidine is its potential as a DNA-binding agent. Bipyrimidine derivatives have been shown to intercalate with DNA, which could make this compound useful in the development of novel anticancer or antibacterial agents. The chlorine atoms and methoxyphenoxy group may further enhance the compound’s DNA-binding properties, potentially leading to the development of new drugs that target DNA replication or transcription.

Additionally, this compound can be explored in materials science, where its bipyrimidine structure can form coordination complexes with transition metals. These complexes can serve as catalysts in organic reactions, with applications in green chemistry and polymer production. The chlorine atoms enhance the compound’s reactivity, making it a valuable ligand for catalytic processes.

As research on 4,6-Dichloro-5-(2-methoxyphenoxy)-2,2'-bipyrimidine progresses, its versatility suggests it may have a wide range of applications, from therapeutic uses to industrial processes. However, challenges remain, particularly in optimizing its bioavailability and reducing potential toxicity. Further studies will be required to refine its structure for specific applications.