Cas no 90358-16-0 (4-chloro-5-methyl-7H-pyrrolo[2,3-d]pyrimidin-2-amine)

4-Chloro-5-methyl-7H-pyrrolo[2,3-d]pyrimidin-2-amine is a heterocyclic compound featuring a pyrrolopyrimidine core, which is of significant interest in medicinal chemistry and pharmaceutical research. Its structure includes a reactive chloro substituent at the 4-position and an amino group at the 2-position, making it a versatile intermediate for further functionalization. The methyl group at the 5-position enhances stability and influences electronic properties. This compound is particularly valuable in the synthesis of kinase inhibitors and other biologically active molecules, owing to its ability to participate in nucleophilic substitution and cross-coupling reactions. Its well-defined reactivity profile and structural features make it a useful building block for drug discovery and development.
4-chloro-5-methyl-7H-pyrrolo[2,3-d]pyrimidin-2-amine structure
90358-16-0 structure
Product Name:4-chloro-5-methyl-7H-pyrrolo[2,3-d]pyrimidin-2-amine
CAS No:90358-16-0
MF:C7H7ClN4
MW:182.610279321671
MDL:MFCD13189356
CID:789015
PubChem ID:5324421
Update Time:2025-06-29

4-chloro-5-methyl-7H-pyrrolo[2,3-d]pyrimidin-2-amine Chemical and Physical Properties

Names and Identifiers

    • 1H-Pyrrolo[2,3-d]pyrimidin-2-amine, 4-chloro-5-methyl-
    • 4-chloro-5-methyl-7H-Pyrrolo[2,3-d]pyrimidin-2-amine
    • SCHEMBL1738453
    • 90358-16-0
    • 2-amino-4-chloro-5-methyl-1h-pyrrolo[2,3-d]pyrimidine
    • PS-20570
    • DTXSID50415908
    • InChI=1/C7H7ClN4/c1-3-2-10-6-4(3)5(8)11-7(9)12-6/h2H,1H3,(H3,9,10,11,12
    • 7H-pyrrolo[2,3-d]pyrimidin-2-amine, 4-chloro-5-methyl-
    • MFCD13189356
    • FT-0708968
    • 4-Chloro-5-methyl-1H-pyrrolo[2,3-d]pyrimidin-2-amine
    • XSTHCQQIOBGYKL-UHFFFAOYSA-N
    • AB68254
    • D97102
    • 4-chloro-5-methyl-7H-pyrrolo[2,3-d]pyrimidin-2-amine
    • MDL: MFCD13189356
    • Inchi: 1S/C7H7ClN4/c1-3-2-10-6-4(3)5(8)11-7(9)12-6/h2H,1H3,(H3,9,10,11,12)
    • InChI Key: XSTHCQQIOBGYKL-UHFFFAOYSA-N
    • SMILES: ClC1=C2C(=NC(N)=N1)NC=C2C

Computed Properties

  • Exact Mass: 182.0359239g/mol
  • Monoisotopic Mass: 182.0359239g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 12
  • Rotatable Bond Count: 0
  • Complexity: 177
  • 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: 1.6
  • Topological Polar Surface Area: 67.6?2

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Additional information on 4-chloro-5-methyl-7H-pyrrolo[2,3-d]pyrimidin-2-amine

Comprehensive Overview of 4-Chloro-5-methyl-7H-pyrrolo[2,3-d]pyrimidin-2-amine (CAS No. 90358-16-0)

The compound 4-Chloro-5-methyl-7H-pyrrolo[2,3-d]pyrimidin-2-amine (CAS No. 90358-16-0) is a heterocyclic organic molecule that has garnered significant attention in pharmaceutical and agrochemical research. Its unique structure, featuring a pyrrolopyrimidine core, makes it a valuable intermediate in the synthesis of bioactive molecules. Researchers are particularly interested in its potential applications in kinase inhibition and cancer therapeutics, aligning with the growing demand for targeted drug discovery.

In recent years, the search for novel small-molecule inhibitors has intensified, driven by advancements in precision medicine. The 4-Chloro-5-methyl-7H-pyrrolo[2,3-d]pyrimidin-2-amine scaffold is often explored due to its ability to modulate key enzymatic pathways. This aligns with trending topics such as personalized cancer treatment and AI-driven drug design, where computational tools predict the efficacy of such compounds. Its chloro and methyl substituents further enhance its reactivity, making it a versatile building block.

From a synthetic chemistry perspective, the compound’s CAS No. 90358-16-0 is frequently referenced in patent literature and academic journals. Its role in constructing ATP-competitive inhibitors is well-documented, addressing the need for kinase-targeted therapies in diseases like rheumatoid arthritis and oncology. The rise of fragment-based drug discovery has also spotlighted this molecule, as its compact size allows for efficient optimization in lead compound development.

Beyond pharmaceuticals, 4-Chloro-5-methyl-7H-pyrrolo[2,3-d]pyrimidin-2-amine finds utility in agrochemical research, particularly in designing herbicides and pesticides with improved selectivity. This resonates with global discussions on sustainable agriculture and eco-friendly pest control, where low-toxicity alternatives are prioritized. The compound’s stability under various conditions further supports its industrial applicability.

Analytical studies of CAS No. 90358-16-0 often highlight its spectroscopic properties, such as NMR and mass spectrometry profiles, which are critical for quality control in manufacturing. The integration of machine learning in chemical analysis has streamlined the characterization of such compounds, a topic frequently searched by chemists and data scientists alike.

In summary, 4-Chloro-5-methyl-7H-pyrrolo[2,3-d]pyrimidin-2-amine represents a multifaceted tool in modern chemistry. Its relevance to drug discovery, agricultural innovation, and computational chemistry ensures its continued prominence in scientific discourse. As research evolves, this compound is poised to play a pivotal role in addressing pressing challenges in health and sustainability.

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