Cas no 1126320-54-4 (2,6-Dichloro-5-methoxy-pyrimidin-4-ylamine)

2,6-Dichloro-5-methoxy-pyrimidin-4-ylamine structure
1126320-54-4 structure
Product Name:2,6-Dichloro-5-methoxy-pyrimidin-4-ylamine
CAS No:1126320-54-4
MF:C5H5Cl2N3O
MW:194.018698453903
CID:2176171
Update Time:2025-07-23

2,6-Dichloro-5-methoxy-pyrimidin-4-ylamine Chemical and Physical Properties

Names and Identifiers

    • 2,6-Dichloro-5-methoxy-4-pyrimidinamine
    • 2,6-dichloro-5-methoxypyrimidin-4-amine
    • 2,6-Dichloro-5-methoxy-pyrimidin-4-ylamine
    • JSJLCTWJWSCECS-UHFFFAOYSA-N
    • 2,6-Dichloro-5-methoxypyrimidin-4-ylamine
    • Inchi: 1S/C5H5Cl2N3O/c1-11-2-3(6)9-5(7)10-4(2)8/h1H3,(H2,8,9,10)
    • InChI Key: JSJLCTWJWSCECS-UHFFFAOYSA-N
    • SMILES: ClC1=C(C(N)=NC(=N1)Cl)OC

Computed Properties

  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 11
  • Rotatable Bond Count: 1
  • Complexity: 137
  • Topological Polar Surface Area: 61

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2,6-Dichloro-5-methoxy-pyrimidin-4-ylamine Related Literature

Additional information on 2,6-Dichloro-5-methoxy-pyrimidin-4-ylamine

Introduction to 2,6-Dichloro-5-methoxy-pyrimidin-4-ylamine (CAS No. 1126320-54-4)

2,6-Dichloro-5-methoxy-pyrimidin-4-ylamine, identified by the Chemical Abstracts Service Number (CAS No.) 1126320-54-4, is a significant intermediate in modern pharmaceutical synthesis. This compound belongs to the pyrimidine class of heterocyclic aromatic organic compounds, characterized by a six-membered ring containing two nitrogen atoms. The presence of chloro and methoxy substituents at the 2nd and 6th positions, respectively, along with an amine group at the 4th position, imparts unique reactivity and makes it a valuable building block in medicinal chemistry.

The structure of 2,6-Dichloro-5-methoxy-pyrimidin-4-ylamine facilitates its use in the development of various bioactive molecules. Its pyrimidine core is a privileged scaffold in drug discovery, frequently incorporated into molecules targeting diseases such as cancer, inflammation, and infectious disorders. The electron-withdrawing nature of the chlorine atoms enhances electrophilicity at specific positions, while the methoxy group introduces steric and electronic modulation. The amine functionality serves as a versatile handle for further chemical modifications via coupling reactions.

In recent years, 2,6-Dichloro-5-methoxy-pyrimidin-4-ylamine has garnered attention in the synthesis of small-molecule inhibitors. Notably, its derivatives have been explored as kinase inhibitors due to the ability of pyrimidine derivatives to mimic ATP binding pockets. For instance, modifications at the 5-position with different substituents have led to compounds exhibiting potent activity against tyrosine kinases involved in tumor proliferation. The synthetic pathways involving 2,6-Dichloro-5-methoxy-pyrimidin-4-ylamine often involve nucleophilic substitution reactions where the chlorine atoms are displaced by pharmacophoric groups.

One of the most compelling applications of this compound is in the field of antiviral research. Pyrimidine-based molecules have demonstrated efficacy against viral enzymes such as polymerases and proteases. Researchers have leveraged the reactivity of 2,6-Dichloro-5-methoxy-pyrimidin-4-ylamine to develop inhibitors targeting RNA-dependent RNA polymerases in viruses like influenza and coronaviruses. The chlorine substituents allow for selective functionalization, enabling the introduction of groups that enhance binding affinity and reduce off-target effects.

The pharmaceutical industry has also utilized 2,6-Dichloro-5-methoxy-pyrimidin-4-ylamine in the development of anti-inflammatory agents. Pyrimidine derivatives modulate inflammatory pathways by inhibiting enzymes such as cyclooxygenase (COX) or lipoxygenase. The structural flexibility of this compound allows chemists to fine-tune its properties for optimal biological activity. For example, studies have shown that replacing one chlorine atom with a hydroxyl group enhances its solubility while maintaining potency against inflammatory cytokines.

Advances in computational chemistry have further accelerated the use of 2,6-Dichloro-5-methoxy-pyrimidin-4-ylamine in drug design. Molecular docking simulations predict favorable interactions between this scaffold and biological targets, guiding rational modifications for improved pharmacokinetics. Additionally, machine learning models trained on experimental data can prioritize synthetic routes that maximize yield and purity. These computational tools are particularly valuable when designing analogs with enhanced selectivity or reduced toxicity.

The agrochemical sector has not been left behind in exploring pyrimidine derivatives like 2,6-Dichloro-5-methoxy-pyrimidin-4-ylamine. Its structural features contribute to the development of novel pesticides that target insect enzymes without harming beneficial organisms. For instance, derivatives have been investigated as acetylcholinesterase inhibitors for controlling pest nervous systems while minimizing environmental impact. Such applications highlight the versatility of this compound beyond human health applications.

In conclusion, 2,6-Dichloro-5-methoxy-pyrimidin-4-ylamine (CAS No. 1126320-54-4) is a multifaceted intermediate with broad utility across pharmaceuticals and agrochemicals. Its unique structural attributes enable diverse modifications for targeting various diseases and pests. As research continues to uncover new therapeutic applications and synthetic methodologies, this compound will remain a cornerstone in medicinal chemistry innovation.

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