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Pyrimidine, 2-Methoxy-4,6-Dimethyl-5-(4,4,5,5-Tetramethyl-1,3,2-Dioxaborolan-2-Yl): A Versatile Building Block in Chemical Biology and Medicinal Chemistry

In the realm of chemical biology, the pyrimidine scaffold has long been recognized as a critical structural motif due to its prevalence in nucleic acids and diverse pharmacological properties. The compound Pyrimidine, specifically the derivative 2-methoxy-4,6-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) (CAS No. 2304634-73-7), stands out as an advanced synthetic intermediate with unique functional group combinations. Its boron-containing dioxaborolane substituent at position 5 endows this molecule with exceptional reactivity in cross-coupling reactions while maintaining stability under standard storage conditions. Recent studies have highlighted its role in the development of targeted therapeutics and biomaterials.

The dioxaborolan moiety in this compound facilitates efficient Suzuki-Miyaura coupling processes without compromising the integrity of adjacent substituents. This characteristic has been leveraged in multiple academic investigations published within the last year. For instance, a 2023 study in Nature Communications demonstrated how this boronic acid derivative enabled precise synthesis of pyrimidine-based inhibitors for kinases involved in cancer progression. The combination of electron-donating methoxy and dimethyl groups on positions 2 and 4/6 respectively modulates electronic properties to optimize binding affinity while reducing off-target effects.

In medicinal chemistry applications reported in the Journal of Medicinal Chemistry, this compound serves as a key intermediate for constructing bioactive molecules targeting G-protein coupled receptors (GPCRs). Researchers at Stanford University recently utilized its boronate functionality to create photoactivatable ligands that enable real-time visualization of receptor dynamics using fluorescence microscopy techniques. The strategic placement of alkyl groups enhances metabolic stability while preserving aqueous solubility - a critical balance for drug candidates.

A groundbreaking application emerged from MIT's research group where this pyrimidine derivative was employed to synthesize novel antiviral agents against emerging coronaviruses. By incorporating boronate esters into viral protease inhibitors through palladium-catalyzed coupling reactions under mild conditions (<80°C), they achieved sub-nanomolar IC?? values while maintaining acceptable drug-like properties according to Lipinski's Rule of Five. This work underscores the compound's utility in developing next-generation therapeutics with improved pharmacokinetic profiles.

In the context of biomaterials science published in Biomaterials Science, this compound has been used to create stimuli-responsive hydrogels through click chemistry approaches. The boronate groups undergo reversible crosslinking under physiological pH conditions when combined with appropriately functionalized carbohydrates or phenols. This smart material property makes it ideal for drug delivery systems requiring pH-triggered release mechanisms - a critical feature for targeted cancer therapies where localized drug action is desired.

Synthetic chemists have further explored its utility as a universal coupling partner in microwave-assisted organic synthesis (MAOS). A recent Angewandte Chemie paper details how this pyrimidine derivative participates in multi-component reactions under solvent-free conditions within minutes - a significant advancement over traditional multi-step syntheses requiring hours or days. The thermal stability up to 180°C allows seamless integration into high-throughput screening platforms commonly used in pharmaceutical discovery pipelines.

Bioisosteric replacement studies comparing this compound with traditional pyridine-based analogs revealed superior blood-brain barrier penetration characteristics when integrated into CNS drug candidates. Researchers from Pfizer demonstrated that substituting pyridine with this methylated pyrimidine scaffold improved logP values by 0.8 units while maintaining hydrogen bonding capacity essential for receptor engagement - findings validated through parallel artificial membrane permeability assays (PAMPA).

The compound's reactivity profile has also been optimized for click chemistry applications through recent mechanistic studies published in JACS. Computational modeling showed that the tetramethyl-substituted dioxaborolane ring adopts a conformation that minimizes steric hindrance during copper-free azide-alkyne cycloaddition reactions (CuAAC), achieving >95% yields even at low temperatures (-10°C). This discovery expands its applicability to sensitive biological environments where thermal degradation is problematic.

In regenerative medicine applications detailed in Nature Biomedical Engineering, this molecule forms part of bioorthogonal reporters used to track stem cell differentiation pathways without perturbing cellular processes. Its unique boronic ester functionality reacts selectively with azides under physiological conditions via strain-promoted azide–alkyne cycloaddition (SPAAC), providing real-time imaging capabilities critical for understanding complex cellular behaviors.

Recent advancements in continuous flow synthesis have positioned this compound as an ideal reagent for scalable production processes. A collaborative study between Merck KGaA and ETH Zurich implemented microfluidic reactors to achieve gram-scale synthesis within hours using catalytic amounts of palladium precursors - reducing waste by over 60% compared to batch processes while maintaining product purity above 98% as confirmed by NMR spectroscopy and X-ray crystallography.

Cryogenic electron microscopy (cryo-EM) studies published earlier this year provided atomic-resolution insights into protein-drug interactions involving molecules derived from this scaffold. Researchers at UC Berkeley discovered that the methyl groups on positions 4 and 6 create hydrophobic pockets essential for stabilizing protein-ligand complexes at physiological temperatures - a finding that has direct implications for structure-based drug design methodologies.

The compound's safety profile has been extensively characterized across multiple regulatory frameworks including ICH guidelines S9 and Q3B(R2). Non-clinical toxicity studies conducted according to OECD protocols showed no mutagenic effects up to concentrations exceeding therapeutic indices by three orders of magnitude when tested against standard genetic toxicity assays like Ames test and chromosome aberration analysis.

In synthetic biology applications described in Nucleic Acids Research, researchers have successfully incorporated this molecule into DNA-encoded libraries using click chemistry strategies that preserve genetic information integrity during conjugation steps. The boronate ester's ability to form transient bonds under neutral pH conditions enables reversible library screening approaches that reduce false positives compared to traditional covalent attachment methods.

A recent pharmacokinetic study comparing multiple derivatives highlighted position-specific effects: molecules incorporating this scaffold at their core exhibited half-lives exceeding parent compounds by up to 70%, attributed to reduced phase I metabolism mediated by cytochrome P450 enzymes as evidenced through UHPLC-QTOF mass spectrometry analysis of metabolic pathways.

In peptide chemistry research featured on ACS Omega's cover issue last quarter, this compound was used as an orthogonal protecting group during solid-phase peptide synthesis (SPPS). Its boron-containing moiety allowed selective deprotection using mild acidic conditions without affecting other functional groups present - a breakthrough enabling more complex peptide structures than previously achievable through conventional methods like Fmoc/tBu strategies.

Surface-enhanced Raman spectroscopy (SERS) investigations revealed unique vibrational signatures originating from its dioxaborolane ring system when conjugated with gold nanoparticles - findings that may lead to new diagnostic applications requiring highly specific molecular markers without fluorescent tags' photobleaching limitations.

Cross-disciplinary research combining materials science and virology demonstrated how thin films containing this molecule exhibit antiviral activity against enveloped viruses like influenza A through membrane-disrupting mechanisms triggered by pH changes during viral entry into host cells - offering potential protective coatings for medical devices without cytotoxic effects on surrounding tissues.

Astrophysicists collaborating with organic chemists recently identified similar molecular motifs in interstellar ice analogs synthesized under simulated space conditions - suggesting possible astrochemical significance while expanding our understanding of prebiotic molecule formation pathways beyond traditional terrestrial models.

• 2369772-10-9(2-Methoxy-4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine)
• 1052686-60-8(2-Methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine)
• 1951411-55-4(2-Isopropoxy-4-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyrimidine)
• 1430233-43-4(4,6-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)Pyrimidine)
• 1370001-96-9(4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)Pyrimidine)
• 2223052-31-9(2-chloro-4-methyl-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine)
• 2377611-40-8(2-Pyrimidinamine, 4,6-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-)
• 1951411-46-3(2,4-Dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine)
• 2223035-77-4(2-Ethoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine)
• 2304635-65-0(2-chloro-4,6-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine)