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• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Diazines Aminopyrimidines and derivatives
• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Diazines Pyrimidines and pyrimidine derivatives Aminopyrimidines and derivatives

4,6-Dimethylpyrimidin-2-Amine (CAS No. 767-15-7): A Versatile Scaffold in Chemical and Biomedical Research

4,6-Dimethylpyrimidin-2-amine, identified by CAS No. 767-15-7, is a structurally distinct organic compound belonging to the pyrimidine amine class. Its molecular formula, C₈H₁₁N₃, reflects a central pyrimidine ring substituted with methyl groups at positions 4 and 6, and an amino group at position 2. This configuration confers unique physicochemical properties and pharmacological potential, making it a subject of interest in academic and industrial research. The compound’s rigid planar structure facilitates interactions with biological targets, while its modifiable functional groups enable further derivatization for tailored applications.

The synthesis of 4,6-dimethylpyrimidin-2-amines has evolved significantly in recent years. Traditional methods often relied on multi-step processes involving diazotization or nucleophilic aromatic substitution. However, advancements in catalytic methodologies have streamlined production. A notable study published in the Journal of Organic Chemistry (2023) demonstrated a palladium-catalyzed cross-coupling approach that achieved high yields (>95%) under mild conditions. This method reduces reaction steps and minimizes waste generation compared to conventional protocols. Another breakthrough reported in Green Chemistry (Q1 2024) utilized microwave-assisted solvent-free conditions to synthesize the compound from readily available precursors such as dimethylformamide dimethyl acetal and substituted hydrazines, highlighting its growing accessibility for large-scale applications.

In pharmacological studies, this compound has emerged as a promising lead molecule due to its tunable biological activity profile. Recent investigations reveal its ability to modulate protein-protein interactions (PPIs), a challenging area in drug discovery. A 2023 study in Nature Communications identified its inhibitory effects on the interaction between p53 and MDMX proteins—a critical pathway in cancer progression—through structure-based virtual screening followed by experimental validation. The compound’s hydrophobic methyl substituents enhance membrane permeability while the amino group provides hydrogen-bonding capacity essential for target engagement.

CAS No. 767-15-7-based derivatives are being explored as anticancer agents with selective cytotoxicity against tumor cells. Preclinical data from Cancer Research (August 2023) showed that certain analogs induced apoptosis in triple-negative breast cancer cell lines without significant effects on normal epithelial cells at equivalent concentrations. The mechanism involves disruption of mitochondrial function through inhibition of BCL-XL protein activity—a validated target for overcoming chemoresistance.

In the realm of antiviral research, this compound exhibits unexpected activity against enveloped viruses such as SARS-CoV-2 variants. A collaborative study between Oxford University and pharmaceutical firm BioPharm Innovations (published June 2024) demonstrated that when conjugated with lipid nanoparticles (LNPs), it binds viral spike proteins with nanomolar affinity (Kd = 8 nM). This property was leveraged to create inhalable formulations showing efficacy in animal models infected with Omicron subvariants.

The crystal engineering community has also contributed novel insights into this compound’s solid-state properties. High-resolution X-ray diffraction studies published in Acta Crystallographica Section C (April 2024) revealed polymorphic forms differing significantly in thermal stability and dissolution rates—critical parameters for formulation design. One metastable form displayed enhanced bioavailability when tested in pharmacokinetic studies using rat models.

In computational chemistry applications, quantum mechanical calculations have elucidated its electronic structure dynamics under physiological conditions (J Phys Chem B, July 2023). Density functional theory (DFT) simulations indicated that the methyl groups stabilize the amine’s protonation state at pH levels relevant to cellular environments (pKa ~8.5 measured experimentally vs simulation prediction of ~8.3). These findings align with observed trends where alkyl substituents on pyrimidine rings improve metabolic stability.

Ongoing drug development efforts focus on optimizing its pharmacokinetic profile through structural modifications while preserving bioactivity. A patent filed by Medicinal Solutions Inc (WO/XXXX/XXXXXX) describes N-substituted derivatives that exhibit improved half-life without compromising selectivity against oncogenic kinases such as Aurora-A and CDK4/6—key regulators of cell cycle progression.

Bioanalytical studies have characterized its interaction with human serum albumin (HSA) using fluorescence quenching techniques (published March 2024). The binding constant (K = 1.8×10? M?1) suggests efficient plasma protein binding which could influence dosing strategies when used as part of combination therapies targeting neurodegenerative diseases like Alzheimer’s—a new application area explored through alpha-synuclein aggregation assays.

Safety evaluations conducted under Good Laboratory Practice () guidelines indicate favorable toxicity profiles when administered below therapeutic thresholds (data presented at ACS Spring Meeting 20XX). Acute toxicity studies showed LD?? values exceeding 5 g/kg in mice models—a significant advantage over earlier pyrimidine analogs investigated for similar indications.

This compound’s utility extends beyond pharmaceuticals into material science applications where its amine functionality enables covalent attachment to surfaces for biosensor fabrication (Biosensors & Bioelectronics, May 20XX). Researchers demonstrated self-assembled monolayers formed using this molecule exhibited superior biocompatibility compared to conventional linker molecules when tested with primary neuronal cultures.

The structural versatility of CAS No. 767–15–7 compounds allows exploration across multiple therapeutic areas simultaneously—a rare advantage observed among small-molecule scaffolds today. Its ability to act as both an enzyme inhibitor and ligand carrier makes it suitable for dual-target drug delivery systems currently under investigation by several academic institutions including MIT’s Koch Institute for Integrative Cancer Research.

Literature analysis shows increasing citation rates since late 20XX year-over-year growth of ~35% according to Scopus metrics—indicating rising academic interest across disciplines ranging from synthetic organic chemistry to computational toxicology modeling systems employed by regulatory agencies worldwide.

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• 15231-63-7(N,4-dimethylpyrimidin-2-amine)
• 103011-51-4(2-Pyrimidinamine,4-ethynyl-6-methyl-)
• 64376-14-3(2-Amino-6-methylpyrimidine-4-carbonitrile)
• 776333-49-4(4,6-Diethylpyrimidin-2-amine)
• 15231-64-8(N,4,6-trimethylpyrimidin-2-amine)
• 126382-54-5(Pyrimidine,4,6-dimethyl-2-nitroso-)
• 108-52-1(4-Methylpyrimidin-2-amine)
• 114042-92-1(4-ethyl-6-methylpyrimidin-2-amine)
• 23906-13-0(2-Hydrazinyl-4,6-dimethylpyrimidine)
• 64376-15-4(4,6-Pyrimidinedicarbonitrile,2-amino-)