Cas no 1289089-91-3 (5-Bromo-2-(4-methylpiperidin-1-yl)pyrimidine)

5-Bromo-2-(4-methylpiperidin-1-yl)pyrimidine is a brominated pyrimidine derivative featuring a 4-methylpiperidine substitution at the 2-position. This compound serves as a versatile intermediate in organic synthesis and pharmaceutical research, particularly in the development of kinase inhibitors and other biologically active molecules. The bromo group at the 5-position offers a reactive site for further functionalization via cross-coupling reactions, such as Suzuki or Buchwald-Hartwig couplings, enabling structural diversification. The 4-methylpiperidine moiety enhances solubility and modulates steric and electronic properties, making it valuable for medicinal chemistry applications. Its well-defined structure and synthetic utility make it a practical choice for targeted molecular design.
5-Bromo-2-(4-methylpiperidin-1-yl)pyrimidine structure
1289089-91-3 structure
Product Name:5-Bromo-2-(4-methylpiperidin-1-yl)pyrimidine
CAS No:1289089-91-3
MF:C10H14BrN3
MW:256.14226102829
MDL:MFCD18840868
CID:4693022
PubChem ID:61036374
Update Time:2025-06-23

5-Bromo-2-(4-methylpiperidin-1-yl)pyrimidine Chemical and Physical Properties

Names and Identifiers

    • 5-bromo-2-(4-methylpiperidin-1-yl)pyrimidine
    • AM86477
    • SCHEMBL23073770
    • 1289089-91-3
    • AKOS010265864
    • N11552
    • MFCD18840868
    • 5-Bromo-2-(4-methylpiperidin-1-yl)pyrimidine
    • MDL: MFCD18840868
    • Inchi: 1S/C10H14BrN3/c1-8-2-4-14(5-3-8)10-12-6-9(11)7-13-10/h6-8H,2-5H2,1H3
    • InChI Key: DGDMWWAUXIIAIC-UHFFFAOYSA-N
    • SMILES: BrC1C=NC(=NC=1)N1CCC(C)CC1

Computed Properties

  • Exact Mass: 255.03711g/mol
  • Monoisotopic Mass: 255.03711g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 14
  • Rotatable Bond Count: 1
  • Complexity: 172
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 29
  • XLogP3: 2.6

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Additional information on 5-Bromo-2-(4-methylpiperidin-1-yl)pyrimidine

Introduction to 5-Bromo-2-(4-methylpiperidin-1-yl)pyrimidine (CAS No. 1289089-91-3) and Its Emerging Applications in Chemical Biology

5-Bromo-2-(4-methylpiperidin-1-yl)pyrimidine, identified by the chemical compound identifier CAS No. 1289089-91-3, is a heterocyclic organic molecule that has garnered significant attention in the field of chemical biology and pharmaceutical research. This compound belongs to the pyrimidine class, a structural motif widely recognized for its biological activity and therapeutic potential. The presence of both bromine and piperidine substituents in its molecular framework endows it with unique chemical properties, making it a valuable scaffold for drug discovery and molecular pharmacology.

The bromine atom in 5-Bromo-2-(4-methylpiperidin-1-yl)pyrimidine serves as a versatile handle for further functionalization through cross-coupling reactions, such as Suzuki-Miyaura, Buchwald-Hartwig, and Negishi couplings. These reactions are fundamental in constructing complex molecular architectures, enabling the synthesis of novel bioactive compounds. The 4-methylpiperidin-1-yl moiety, on the other hand, contributes to the compound's solubility and metabolic stability, which are critical factors in drug development. The combination of these structural features makes 5-Bromo-2-(4-methylpiperidin-1-yl)pyrimidine a promising candidate for exploring new therapeutic avenues.

Recent advancements in medicinal chemistry have highlighted the importance of pyrimidine derivatives in addressing various diseases, including cancer, infectious disorders, and neurological conditions. The pyrimidine core is a key component in several FDA-approved drugs, such as acyclovir and ganciclovir, which are used to treat viral infections. The introduction of halogenated pyrimidines has further expanded their utility by enhancing binding affinity and selectivity towards biological targets.

In the context of oncology research, 5-Bromo-2-(4-methylpiperidin-1-yl)pyrimidine has been investigated for its potential role in modulating kinase enzymes that are overexpressed in cancer cells. Kinases play a crucial role in cell signaling pathways, and their dysregulation is often associated with tumorigenesis. By designing molecules that selectively inhibit aberrant kinase activity, researchers aim to develop more effective anticancer therapies with reduced side effects. Preliminary studies have demonstrated that derivatives of this compound exhibit inhibitory effects on certain kinases, suggesting their therapeutic relevance.

The molecular design of 5-Bromo-2-(4-methylpiperidin-1-yl)pyrimidine allows for fine-tuning its pharmacokinetic properties through structural modifications. For instance, optimizing the piperidine ring can enhance oral bioavailability and tissue penetration, while altering the bromine substitution pattern can improve target specificity. These considerations are essential for translating preclinical findings into clinical applications.

Another area where this compound shows promise is in the development of antiviral agents. The bromine atom facilitates the introduction of diverse functional groups, enabling the creation of molecules that can interact with viral enzymes or receptors. Such interactions are critical for disrupting viral replication cycles and preventing disease progression. Current research is exploring how modifications to the pyrimidine scaffold can enhance antiviral efficacy against emerging pathogens.

The synthesis of 5-Bromo-2-(4-methylpiperidin-1-yl)pyrimidine involves multi-step organic transformations that require precise control over reaction conditions. Advanced synthetic methodologies have been employed to achieve high yields and purity levels, ensuring that subsequent biological evaluations are conducted on well-characterized samples. Techniques such as high-performance liquid chromatography (HPLC), nuclear magnetic resonance (NMR) spectroscopy, and mass spectrometry (MS) are routinely used to confirm molecular structure and assess sample integrity.

In conclusion, 5-Bromo-2-(4-methylpiperidin-1-yl)pyrimidine (CAS No. 1289089-91-3) represents a significant advancement in medicinal chemistry due to its versatile structural features and potential therapeutic applications. Its role in drug discovery spans multiple disease areas, underscoring its importance as a molecular building block. As research continues to uncover new biological targets and synthetic strategies, compounds like this will remain at the forefront of innovation in chemical biology.

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