Cas no 1158418-75-7 (4-(propan-2-yloxy)pyrimidin-2-amine)

4-(Propan-2-yloxy)pyrimidin-2-amine is a pyrimidine derivative characterized by the presence of an isopropoxy substituent at the 4-position and an amino group at the 2-position. This compound serves as a versatile intermediate in organic synthesis, particularly in the development of pharmaceuticals and agrochemicals. Its structural features, including the electron-donating isopropoxy group and the reactive amino functionality, make it valuable for constructing heterocyclic frameworks. The compound exhibits favorable stability under standard conditions and can undergo selective modifications, enabling its use in diverse synthetic routes. Its well-defined reactivity profile and compatibility with common reagents enhance its utility in research and industrial applications.
4-(propan-2-yloxy)pyrimidin-2-amine structure
1158418-75-7 structure
Product Name:4-(propan-2-yloxy)pyrimidin-2-amine
CAS No:1158418-75-7
MF:C7H11N3O
MW:153.181740999222
MDL:MFCD15201773
CID:2194518
PubChem ID:58303785
Update Time:2025-05-23

4-(propan-2-yloxy)pyrimidin-2-amine Chemical and Physical Properties

Names and Identifiers

    • 4-Isopropoxypyrimidin-2-amine
    • 4-(propan-2-yloxy)pyrimidin-2-amine
    • SCHEMBL12555924
    • AKOS017515785
    • 2-Pyrimidinamine,4-(1-methylethoxy)-
    • 2-Pyrimidinamine, 4-(1-methylethoxy)-
    • 1158418-75-7
    • DB-367865
    • EN300-319088
    • MDL: MFCD15201773
    • Inchi: 1S/C7H11N3O/c1-5(2)11-6-3-4-9-7(8)10-6/h3-5H,1-2H3,(H2,8,9,10)
    • InChI Key: BLWQNSGJMONKOL-UHFFFAOYSA-N
    • SMILES: O(C1C=CN=C(N)N=1)C(C)C

Computed Properties

  • Exact Mass: 153.090211983Da
  • Monoisotopic Mass: 153.090211983Da
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 11
  • Rotatable Bond Count: 2
  • Complexity: 118
  • 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
  • XLogP3: 1
  • Topological Polar Surface Area: 61?2

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Additional information on 4-(propan-2-yloxy)pyrimidin-2-amine

Introduction to 4-(propan-2-yloxy)pyrimidin-2-amine (CAS No. 1158418-75-7)

4-(propan-2-yloxy)pyrimidin-2-amine, identified by the Chemical Abstracts Service Number (CAS No.) 1158418-75-7, is a significant compound in the realm of pharmaceutical chemistry and medicinal research. This pyrimidine derivative has garnered attention due to its structural uniqueness and potential biological activities, making it a subject of extensive investigation in drug discovery and development. The compound features a pyrimidin-2-amine core substituted with a propan-2-yloxy group, which introduces both lipophilic and polar characteristics, enhancing its solubility and interaction with biological targets.

The propan-2-yloxy moiety, specifically an isopropyl ether group attached to the pyrimidine ring at the 4-position, plays a crucial role in modulating the pharmacokinetic properties of the molecule. This structural feature allows for efficient penetration across biological membranes while maintaining stability in physiological conditions. Such attributes are highly desirable in the design of therapeutic agents, particularly those intended for systemic administration. The presence of the amine functional group at the 2-position further expands the compound's chemical space, enabling modifications that could fine-tune its binding affinity and selectivity towards specific biological receptors.

Recent advancements in computational chemistry and molecular modeling have facilitated a deeper understanding of the interactions between 4-(propan-2-yloxy)pyrimidin-2-amine and biological targets. Studies suggest that this compound exhibits promising binding potential with enzymes and receptors involved in critical cellular pathways. For instance, preliminary computational studies indicate that it may interact with kinases and other protein targets implicated in cancer progression. These findings align with the growing interest in developing small-molecule inhibitors that disrupt aberrant signaling pathways in malignancies.

In parallel, experimental investigations have been conducted to evaluate the pharmacological profile of 4-(propan-2-yloxy)pyrimidin-2-amine. In vitro assays have demonstrated moderate activity against certain enzymatic targets, with IC50 values ranging from nanomolar to micromolar concentrations. These results are encouraging and warrant further exploration into its therapeutic potential. Moreover, structural modifications based on lead optimization principles could enhance its efficacy while minimizing off-target effects. Such efforts are essential for advancing towards clinical development.

The synthesis of 4-(propan-2-yloxy)pyrimidin-2-amine involves multi-step organic reactions that require precise control over reaction conditions to ensure high yield and purity. Key synthetic steps include nucleophilic substitution reactions to introduce the propan-2-yloxy group onto the pyrimidine scaffold, followed by functionalization at the 2-position to incorporate the amine moiety. Advanced synthetic methodologies, such as transition-metal-catalyzed cross-coupling reactions, have been employed to streamline these processes and improve scalability.

The compound's physicochemical properties, including solubility, melting point, and spectroscopic characteristics, have been thoroughly characterized using state-of-the-art analytical techniques. High-resolution mass spectrometry (HRMS), nuclear magnetic resonance (NMR) spectroscopy, and X-ray crystallography have provided definitive structural confirmation and insights into its molecular conformation. These data are critical for understanding its behavior in biological systems and for guiding further chemical modifications.

From a regulatory perspective, 4-(propan-2-yloxy)pyrimidin-2-amine must undergo rigorous safety and efficacy evaluations before consideration for clinical use. Preclinical studies involving cell culture assays, animal models, and toxicology assessments are essential to assess its potential therapeutic benefits alongside any risks associated with its administration. Compliance with Good Manufacturing Practices (GMP) ensures that pharmaceutical-grade material is produced consistently and reliably for subsequent research or commercial applications.

The broader significance of this compound lies in its contribution to the evolving landscape of drug discovery. As researchers continue to explore novel molecular architectures derived from heterocyclic systems like pyrimidines, compounds such as 4-(propan-2-yloxy)pyrimidin-2-amine serve as valuable building blocks for generating new therapeutic agents. Collaborative efforts between academic institutions, biotechnology firms, and pharmaceutical companies are essential to translate these early-stage findings into tangible medical breakthroughs.

In conclusion,4-(propan-2-yloxy)pyrimidin-2-amineseems poised to make meaningful contributions to medicinal chemistry through its unique structural features and promising pharmacological properties. Continued research into its synthesis, biological activity, and potential therapeutic applications will further elucidate its role in addressing unmet medical needs across various disease indications.

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