Cas no 2223042-99-5 (2-Amino-4-ethylpyrimidine-5-boronic acid pinacol ester)

2-Amino-4-ethylpyrimidine-5-boronic acid pinacol ester is a boronic acid derivative commonly employed in Suzuki-Miyaura cross-coupling reactions, a pivotal method for forming carbon-carbon bonds in synthetic organic chemistry. The pinacol ester group enhances stability, improving handling and storage compared to its free boronic acid counterpart. The amino and ethyl substituents on the pyrimidine ring contribute to its reactivity and selectivity in coupling reactions, making it a valuable intermediate in pharmaceutical and agrochemical synthesis. Its compatibility with diverse reaction conditions and functional groups underscores its utility in constructing complex heterocyclic frameworks. This compound is particularly advantageous for applications requiring precise molecular modifications.
2-Amino-4-ethylpyrimidine-5-boronic acid pinacol ester structure
2223042-99-5 structure
Product Name:2-Amino-4-ethylpyrimidine-5-boronic acid pinacol ester
CAS No:2223042-99-5
MF:C12H20BN3O2
MW:249.12
CID:5144582
PubChem ID:90234004
Update Time:2025-10-28

2-Amino-4-ethylpyrimidine-5-boronic acid pinacol ester Chemical and Physical Properties

Names and Identifiers

    • 2-Amino-4-ethylpyrimidine-5-boronic acid pinacol ester
    • 4-Ethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-amine
    • 2223042-99-5
    • SCHEMBL15814443
    • Inchi: 1S/C12H20BN3O2/c1-6-9-8(7-15-10(14)16-9)13-17-11(2,3)12(4,5)18-13/h7H,6H2,1-5H3,(H2,14,15,16)
    • InChI Key: RXEYFUGOFSMZDE-UHFFFAOYSA-N
    • SMILES: C1(N)=NC=C(B2OC(C)(C)C(C)(C)O2)C(CC)=N1

Computed Properties

  • Exact Mass: 249.1648571g/mol
  • Monoisotopic Mass: 249.1648571g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 5
  • Heavy Atom Count: 18
  • Rotatable Bond Count: 2
  • Complexity: 296
  • 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: 70.3?2

2-Amino-4-ethylpyrimidine-5-boronic acid pinacol ester Pricemore >>

Related Categories No. Product Name Cas No. Purity Specification Price update time Inquiry
SHANG HAI MAI KE LIN SHENG HUA Technology Co., Ltd.
A907921-5mg
2-Amino-4-ethylpyrimidine-5-boronic acid pinacol ester
2223042-99-5 95%
5mg
¥1,008.00 2022-09-29
SHANG HAI MAI KE LIN SHENG HUA Technology Co., Ltd.
A907921-25mg
2-Amino-4-ethylpyrimidine-5-boronic acid pinacol ester
2223042-99-5 95%
25mg
¥2,930.40 2022-09-29

Additional information on 2-Amino-4-ethylpyrimidine-5-boronic acid pinacol ester

Introduction to 2-Amino-4-ethylpyrimidine-5-boronic acid pinacol ester (CAS No. 2223042-99-5)

2-Amino-4-ethylpyrimidine-5-boronic acid pinacol ester, identified by the chemical compound code CAS No. 2223042-99-5, is a significant intermediate in the field of pharmaceutical and agrochemical research. This compound belongs to the pyrimidine class, which is well-documented for its broad spectrum of biological activities and utility in drug development. The boronic acid pinacol ester moiety enhances its reactivity, making it a valuable building block in Suzuki-Miyaura cross-coupling reactions—a cornerstone of modern organic synthesis.

The structure of 2-amino-4-ethylpyrimidine-5-boronic acid pinacol ester consists of a pyrimidine ring substituted with an amino group at the 2-position, an ethyl group at the 4-position, and a boronic acid pinacol ester at the 5-position. This specific arrangement imparts unique chemical properties that make it particularly useful in medicinal chemistry. The presence of the amino group allows for further functionalization via reductive amination or acylation, while the boronic ester functionality facilitates palladium-catalyzed coupling reactions with aryl or vinyl halides, enabling the construction of more complex molecular architectures.

In recent years, there has been growing interest in pyrimidine derivatives due to their demonstrated efficacy as kinase inhibitors, antiviral agents, and antimicrobial compounds. The compound CAS No. 2223042-99-5 has emerged as a key intermediate in synthesizing novel therapeutic agents targeting various diseases. For instance, researchers have leveraged its reactivity to develop inhibitors of Janus kinases (JAKs), which play a crucial role in inflammatory pathways. By incorporating this compound into drug candidates, scientists aim to modulate these pathways with high selectivity and reduced side effects.

One notable application of 2-amino-4-ethylpyrimidine-5-boronic acid pinacol ester is in the synthesis of antiviral drugs. Pyrimidine-based molecules have shown promise against viruses such as hepatitis C and human immunodeficiency virus (HIV). The boronic ester group enables efficient coupling with other fragments through cross-coupling reactions, allowing for the rapid assembly of complex pharmacophores. This capability is particularly valuable in high-throughput screening programs where large libraries of compounds need to be generated and tested for biological activity.

The pharmaceutical industry has also explored this compound for its potential in oncology research. Pyrimidine derivatives are known to interfere with DNA replication and repair mechanisms in cancer cells, making them attractive candidates for developing chemotherapeutic agents. For example, modifications of CAS No. 2223042-99-5 have been investigated as inhibitors of polo-like kinases (PLKs), which are overexpressed in many tumor types. By designing analogs with enhanced solubility or bioavailability, researchers hope to improve treatment outcomes for patients with solid tumors or hematological malignancies.

Advances in computational chemistry have further accelerated the use of 2-amino-4-ethylpyrimidine-5-boronic acid pinacol ester in drug discovery. Molecular modeling techniques allow researchers to predict how different substituents will affect the compound's binding affinity and pharmacokinetic properties before conducting expensive wet-lab experiments. This approach has led to more efficient synthesis routes and reduced time-to-market for new therapeutics. Additionally, green chemistry principles are being integrated into these processes, minimizing waste and improving sustainability—a critical consideration in modern pharmaceutical development.

The agrochemical sector has not been left behind in exploring the potential of pyrimidine derivatives like CAS No. 2223042-99-5. These compounds have been investigated as leads for novel herbicides and fungicides due to their ability to disrupt essential metabolic pathways in pests and weeds while maintaining low toxicity to non-target organisms. By tailoring the substituents on the pyrimidine core, chemists can fine-tune the selectivity and environmental profile of these agrochemicals, addressing growing concerns about pesticide resistance and ecological impact.

Future directions in the study of 2-amino-4-ethylpyrimidine-5-boronic acid pinacol ester include exploring its role in developing next-generation therapeutics targeting emerging infectious diseases and chronic conditions. The versatility of this intermediate makes it an indispensable tool for medicinal chemists seeking to address unmet medical needs. As synthetic methodologies continue to evolve—particularly those involving transition-metal catalysis—the utility of boronic acid pinacol esters is expected to expand even further.

In conclusion,CAS No 2223042 -99 -5 represents a pivotal compound in synthetic organic chemistry with far-reaching implications across multiple industries. Its unique structural features enable diverse applications ranging from drug development to sustainable agriculture,underscoring its importance as a research tool today and tomorrow,while driving innovation across scientific disciplines.

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