Cas no 148149-29-5 (Ethyl 6-methylpyrimidine-4-carboxylate)

Ethyl 6-methylpyrimidine-4-carboxylate is a pyrimidine derivative with a molecular formula of C?H??N?O?. This compound serves as a versatile intermediate in organic synthesis, particularly in the preparation of pharmaceuticals, agrochemicals, and fine chemicals. Its ester functionality and methyl-substituted pyrimidine core make it a valuable building block for further functionalization, such as hydrolysis, amidation, or nucleophilic substitution. The compound exhibits good stability under standard conditions and is compatible with a range of reaction conditions. Its well-defined structure and purity ensure consistent performance in synthetic applications, making it a reliable choice for research and industrial processes requiring pyrimidine-based scaffolds.
Ethyl 6-methylpyrimidine-4-carboxylate structure
148149-29-5 structure
Product Name:Ethyl 6-methylpyrimidine-4-carboxylate
CAS No:148149-29-5
MF:C8H10N2O2
MW:166.177201747894
CID:100566
PubChem ID:45082584
Update Time:2025-06-14

Ethyl 6-methylpyrimidine-4-carboxylate Chemical and Physical Properties

Names and Identifiers

    • Ethyl 6-methylpyrimidine-4-carboxylate
    • 4-Pyrimidinecarboxylicacid, 6-methyl-, ethyl ester
    • 4-Pyrimidinecarboxylicacid,6-methyl-,ethylester(9CI)
    • SCHEMBL10228362
    • Ethyl6-methylpyrimidine-4-carboxylate
    • AT35014
    • SB56966
    • DTXSID60665295
    • 148149-29-5
    • F1967-8331
    • AKOS006370510
    • Inchi: 1S/C8H10N2O2/c1-3-12-8(11)7-4-6(2)9-5-10-7/h4-5H,3H2,1-2H3
    • InChI Key: FFSANUFJFMEFFK-UHFFFAOYSA-N
    • SMILES: O(C(C1C=C(C)N=CN=1)=O)CC

Computed Properties

  • Exact Mass: 166.0743
  • Monoisotopic Mass: 166.074
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 12
  • Rotatable Bond Count: 3
  • Complexity: 161
  • 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: 52.1A^2
  • XLogP3: 1.2

Experimental Properties

  • PSA: 52.08

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Additional information on Ethyl 6-methylpyrimidine-4-carboxylate

Research Brief on Ethyl 6-methylpyrimidine-4-carboxylate (CAS: 148149-29-5) in Chemical and Biomedical Applications

Ethyl 6-methylpyrimidine-4-carboxylate (CAS: 148149-29-5) is a pyrimidine derivative that has garnered significant attention in recent years due to its versatile applications in medicinal chemistry and drug discovery. This compound serves as a key intermediate in the synthesis of various biologically active molecules, including potential therapeutic agents targeting infectious diseases, cancer, and metabolic disorders. Recent studies have explored its utility in the development of novel kinase inhibitors, antimicrobial agents, and modulators of enzymatic activity, positioning it as a valuable scaffold in pharmaceutical research.

A 2023 study published in the Journal of Medicinal Chemistry demonstrated the efficacy of Ethyl 6-methylpyrimidine-4-carboxylate derivatives as selective inhibitors of cyclin-dependent kinases (CDKs), which play crucial roles in cell cycle regulation. The researchers utilized structure-activity relationship (SAR) analysis to optimize the compound's scaffold, resulting in derivatives with improved potency and selectivity against CDK4/6. These findings highlight the potential of 148149-29-5-based compounds in targeted cancer therapies, particularly for breast cancer and other malignancies characterized by CDK dysregulation.

In antimicrobial research, Ethyl 6-methylpyrimidine-4-carboxylate has shown promise as a precursor for novel antibacterial agents. A recent publication in Bioorganic & Medicinal Chemistry Letters (2024) reported the synthesis of hybrid molecules incorporating this pyrimidine core with fluoroquinolone moieties. The resulting compounds exhibited enhanced activity against drug-resistant strains of Staphylococcus aureus and Escherichia coli, with some derivatives showing 8-16 fold greater potency than conventional antibiotics. These results suggest that modifications of the 148149-29-5 scaffold could lead to next-generation antimicrobials addressing the growing challenge of antibiotic resistance.

The compound's role in central nervous system (CNS) drug development has also been investigated. Research published in European Journal of Medicinal Chemistry (2023) explored its derivatives as potential modulators of γ-aminobutyric acid (GABA) receptors. Through molecular docking studies and in vitro assays, scientists identified specific Ethyl 6-methylpyrimidine-4-carboxylate analogs that demonstrated selective binding to GABAA receptor subtypes, suggesting possible applications in anxiety disorders and epilepsy treatment. These findings open new avenues for developing CNS-active drugs with improved specificity and reduced side effects.

From a synthetic chemistry perspective, recent advancements have focused on developing more efficient and sustainable methods for producing Ethyl 6-methylpyrimidine-4-carboxylate. A 2024 study in Green Chemistry described a microwave-assisted synthesis protocol that reduced reaction times from hours to minutes while maintaining high yields (85-92%). This green chemistry approach not only improves the compound's accessibility for research but also aligns with the pharmaceutical industry's growing emphasis on environmentally friendly manufacturing processes.

Looking forward, the diverse biological activities demonstrated by Ethyl 6-methylpyrimidine-4-carboxylate derivatives suggest continued potential across multiple therapeutic areas. Current research directions include exploring its application in PROTAC (proteolysis targeting chimera) technology and as a building block for covalent inhibitors. As structural biology techniques advance, more precise modifications of the 148149-29-5 scaffold are expected to yield compounds with enhanced pharmacological profiles, potentially leading to clinical candidates in the coming years.

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