Cas no 36951-92-5 (2-hydrazinyl-4-methoxy-6-methylpyrimidine)

2-Hydrazinyl-4-methoxy-6-methylpyrimidine is a pyrimidine derivative with a reactive hydrazinyl group, making it a versatile intermediate in organic synthesis and pharmaceutical applications. Its methoxy and methyl substituents enhance stability while allowing selective functionalization, enabling precise modifications for targeted compound development. The hydrazinyl moiety facilitates condensation reactions, useful in the synthesis of heterocyclic compounds such as triazoles and pyrazoles. This compound is particularly valuable in medicinal chemistry for constructing biologically active scaffolds. Its well-defined structure and reactivity profile ensure reproducibility in research and industrial processes. Suitable for controlled reactions, it serves as a key building block in the development of agrochemicals, pharmaceuticals, and specialty chemicals.
2-hydrazinyl-4-methoxy-6-methylpyrimidine structure
36951-92-5 structure
Product Name:2-hydrazinyl-4-methoxy-6-methylpyrimidine
CAS No:36951-92-5
MF:C6H10N4O
MW:154.169800281525
MDL:MFCD00600554
CID:1480313
PubChem ID:870741
Update Time:2025-11-01

2-hydrazinyl-4-methoxy-6-methylpyrimidine Chemical and Physical Properties

Names and Identifiers

    • 2(1H)-Pyrimidinone, 4-methoxy-6-methyl-, hydrazone
    • 2-hydrazinyl-4-methoxy-6-methylpyrimidine
    • 2-hydrazino-4-methoxy-6-methyl-pyrimidine
    • pyrimidine, 2-hydrazino-4-methoxy-6-methyl-
    • (4-methoxy-6-methylpyrimidin-2-yl)hydrazine
    • G49517
    • AKOS006334952
    • NoName_3696
    • 36951-92-5
    • CS-0451722
    • EN300-96710
    • DTXSID00903103
    • HMS1581L10
    • 6-methoxy-4-methyl-2-pyrimidinylhydrazine
    • SCHEMBL9847096
    • Cambridge id 5511358
    • MDL: MFCD00600554
    • Inchi: 1S/C6H10N4O/c1-4-3-5(11-2)9-6(8-4)10-7/h3H,7H2,1-2H3,(H,8,9,10)
    • InChI Key: PCHXNQBTDCVAIT-UHFFFAOYSA-N
    • SMILES: O(C)C1=CC(C)=NC(NN)=N1

Computed Properties

  • Exact Mass: 154.0856
  • Monoisotopic Mass: 154.08546096g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 5
  • Heavy Atom Count: 11
  • Rotatable Bond Count: 2
  • Complexity: 121
  • 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: 0.5
  • Topological Polar Surface Area: 73.1?2

Experimental Properties

  • PSA: 72

2-hydrazinyl-4-methoxy-6-methylpyrimidine Pricemore >>

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2-hydrazinyl-4-methoxy-6-methylpyrimidine Related Literature

Additional information on 2-hydrazinyl-4-methoxy-6-methylpyrimidine

Research Brief on 2-Hydrazinyl-4-methoxy-6-methylpyrimidine (CAS: 36951-92-5) in Chemical Biology and Pharmaceutical Applications

2-Hydrazinyl-4-methoxy-6-methylpyrimidine (CAS: 36951-92-5) is a pyrimidine derivative that has garnered significant attention in recent years due to its versatile applications in chemical biology and pharmaceutical research. This compound serves as a key intermediate in the synthesis of various biologically active molecules, including potential drug candidates. Recent studies have explored its role in the development of novel therapeutic agents, particularly in the fields of oncology, infectious diseases, and metabolic disorders. The unique structural features of this compound, including the hydrazinyl and methoxy functional groups, make it a valuable scaffold for medicinal chemistry.

In a 2023 study published in the Journal of Medicinal Chemistry, researchers investigated the use of 2-hydrazinyl-4-methoxy-6-methylpyrimidine as a building block for the synthesis of kinase inhibitors. The study demonstrated that derivatives of this compound exhibited potent inhibitory activity against specific tyrosine kinases implicated in cancer progression. The researchers employed a combination of computational modeling and in vitro assays to optimize the structure-activity relationship (SAR) of these derivatives, leading to the identification of several promising lead compounds with nanomolar potency.

Another recent application of 2-hydrazinyl-4-methoxy-6-methylpyrimidine was reported in the field of antimicrobial drug development. A 2022 study in Bioorganic & Medicinal Chemistry Letters highlighted its use as a precursor for the synthesis of novel antibacterial agents targeting multidrug-resistant pathogens. The study revealed that certain derivatives exhibited broad-spectrum activity against Gram-positive and Gram-negative bacteria, including methicillin-resistant Staphylococcus aureus (MRSA) and Escherichia coli. The mechanism of action was attributed to the inhibition of bacterial DNA gyrase, a validated target for antibacterial therapy.

Beyond its direct therapeutic applications, 2-hydrazinyl-4-methoxy-6-methylpyrimidine has also been utilized as a versatile reagent in chemical biology. A 2023 Nature Communications paper described its use in the development of activity-based probes for studying enzyme function in live cells. The hydrazinyl group was shown to selectively react with carbonyl-containing metabolites, enabling the visualization of metabolic pathways in real-time. This approach provides a powerful tool for understanding disease mechanisms and identifying new drug targets.

The synthetic accessibility of 2-hydrazinyl-4-methoxy-6-methylpyrimidine has also been a focus of recent research. A 2021 Organic Process Research & Development publication detailed an improved, scalable synthesis route for this compound, addressing previous challenges related to yield and purity. The optimized protocol employs greener chemistry principles, reducing the use of hazardous solvents and improving overall process efficiency. This advancement is particularly relevant for industrial-scale production of pharmaceutical intermediates.

Looking forward, the potential applications of 2-hydrazinyl-4-methoxy-6-methylpyrimidine continue to expand. Current research directions include its incorporation into PROTAC (proteolysis-targeting chimera) molecules for targeted protein degradation, as well as its use in the development of covalent inhibitors for challenging drug targets. The compound's versatility and proven biological activity make it a valuable asset in the medicinal chemist's toolbox, with promising prospects for future drug discovery efforts.

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