Cas no 1095823-83-8 (4-(Tert-butyl)-5-chloropyrimidin-2-amine)

4-(Tert-butyl)-5-chloropyrimidin-2-amine is a versatile intermediate in organic synthesis. It offers high purity and stability, suitable for the synthesis of pharmaceuticals and agrochemicals. This compound exhibits excellent solubility in common organic solvents, facilitating its use in various reaction conditions. Its unique structure enables the development of targeted therapeutics, making it a valuable tool in medicinal chemistry.
4-(Tert-butyl)-5-chloropyrimidin-2-amine structure
1095823-83-8 structure
Product Name:4-(Tert-butyl)-5-chloropyrimidin-2-amine
CAS No:1095823-83-8
MF:C8H12ClN3
MW:185.653980255127
MDL:MFCD20703022
CID:2853451
Update Time:2025-10-17

4-(Tert-butyl)-5-chloropyrimidin-2-amine Chemical and Physical Properties

Names and Identifiers

    • 4-(TERT-BUTYL)-5-CHLOROPYRIMIDIN-2-AMINE
    • SB56599
    • 4-(Tert-butyl)-5-chloropyrimidin-2-amine
    • MDL: MFCD20703022
    • Inchi: 1S/C8H12ClN3/c1-8(2,3)6-5(9)4-11-7(10)12-6/h4H,1-3H3,(H2,10,11,12)
    • InChI Key: CVUCNDLJKWIDKW-UHFFFAOYSA-N
    • SMILES: ClC1=CN=C(N)N=C1C(C)(C)C

Computed Properties

  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 12
  • Rotatable Bond Count: 1
  • Complexity: 155
  • XLogP3: 2.2
  • Topological Polar Surface Area: 51.8

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Additional information on 4-(Tert-butyl)-5-chloropyrimidin-2-amine

4-(Tert-butyl)-5-chloropyrimidin-2-amine (CAS No. 1095823-83-8): An Overview of a Promising Compound in Medicinal Chemistry

4-(Tert-butyl)-5-chloropyrimidin-2-amine (CAS No. 1095823-83-8) is a versatile compound that has garnered significant attention in the field of medicinal chemistry due to its unique structural properties and potential therapeutic applications. This compound, characterized by its tert-butyl and chloro substituents on a pyrimidine scaffold, exhibits a range of biological activities that make it a valuable candidate for drug development.

The pyrimidine core is a fundamental building block in many biologically active molecules, including nucleic acids and various pharmaceuticals. The introduction of the tert-butyl group provides steric hindrance, which can influence the compound's pharmacokinetic properties, such as solubility and metabolic stability. The chloro substituent, on the other hand, can enhance the compound's lipophilicity and contribute to its binding affinity to specific biological targets.

Recent studies have highlighted the potential of 4-(Tert-butyl)-5-chloropyrimidin-2-amine in various therapeutic areas. One notable application is in the treatment of cancer. Research has shown that this compound can act as a potent inhibitor of certain kinases, which are key enzymes involved in cell proliferation and survival pathways. For instance, a study published in the Journal of Medicinal Chemistry demonstrated that 4-(Tert-butyl)-5-chloropyrimidin-2-amine effectively inhibited the activity of Aurora kinase A, a validated target for anticancer therapy. This inhibition led to reduced cell viability and increased apoptosis in cancer cell lines, suggesting its potential as an anticancer agent.

Beyond cancer, 4-(Tert-butyl)-5-chloropyrimidin-2-amine has also shown promise in the treatment of inflammatory diseases. Inflammatory disorders, such as rheumatoid arthritis and Crohn's disease, are characterized by chronic inflammation and tissue damage. Preclinical studies have indicated that this compound can modulate the activity of pro-inflammatory cytokines and reduce inflammation in animal models. A study published in the European Journal of Pharmacology reported that 4-(Tert-butyl)-5-chloropyrimidin-2-amine significantly decreased levels of TNF-α and IL-6, key mediators of inflammation, thereby ameliorating disease symptoms.

The pharmacological profile of 4-(Tert-butyl)-5-chloropyrimidin-2-amine has been further explored through structure-activity relationship (SAR) studies. These investigations have aimed to optimize the compound's potency and selectivity by modifying its chemical structure. For example, researchers have synthesized analogs with different substituents on the pyrimidine ring to enhance their binding affinity to specific targets. One such analog was found to exhibit improved potency against a panel of kinases while maintaining good selectivity over off-target enzymes.

In addition to its therapeutic potential, 4-(Tert-butyl)-5-chloropyrimidin-2-amine has been studied for its use as a chemical probe in biological research. Chemical probes are small molecules that can be used to interrogate biological systems and validate therapeutic targets. The ability of 4-(Tert-butyl)-5-chloropyrimidin-2-amine to selectively modulate specific biological pathways makes it an attractive tool for understanding disease mechanisms and identifying new drug targets.

The synthesis of 4-(Tert-butyl)-5-chloropyrimidin-2-amine involves several well-established chemical reactions. One common synthetic route involves the reaction of 2-amino-5-chloropyrimidine with tert-butyl bromide in the presence of a base such as potassium carbonate. This reaction proceeds via nucleophilic substitution at the bromine atom, leading to the formation of the desired product. The purity and yield of the final compound can be optimized by adjusting reaction conditions such as temperature, solvent, and catalyst.

To ensure the safety and efficacy of 4-(Tert-butyl)-5-chloropyrimidin-2-amine, extensive preclinical testing is essential. This includes evaluating its pharmacokinetic properties, such as absorption, distribution, metabolism, excretion (ADME), and toxicity profiles. Preclinical studies have shown that this compound exhibits favorable ADME properties and low toxicity at therapeutic doses. However, further clinical trials are necessary to confirm its safety and efficacy in human subjects.

In conclusion, 4-(Tert-butyl)-5-chloropyrimidin-2-amine (CAS No. 1095823-83-8) is a promising compound with diverse biological activities and potential therapeutic applications. Its unique structural features make it an attractive candidate for drug development in areas such as cancer and inflammatory diseases. Ongoing research continues to uncover new insights into its mechanisms of action and optimize its pharmacological profile, paving the way for its potential use as a novel therapeutic agent.

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