- Chemical Profile and Properties of 6-Amino-1,3-Dimethyluracil
- Technical Advantages and Superior Synthesis Pathways
- Vendor Comparison: Key Differentiators Explored
- Custom Synthesis Options for Specialized Applications
- Industrial Applications: Agrochemicals to Neuropharmacology
- Quality Control: Analytical Methods and Certification
- Future Outlook for 6-Amino-1,3-Dimethyluracil Innovations
(6-amino-1,3-dimethyluracil)
Understanding 6-Amino-1,3-Dimethyluracil Fundamentals
6-Amino-1,3-dimethyluracil (CAS 31437-42-0) serves as a crucial heterocyclic building block with molecular formula C6H9N3O2. Its structural configuration – featuring amino and methyl substituents at the uracil core – enables unique hydrogen-bonding capabilities essential for pharmaceutical bioactivity. Recent studies indicate superior thermal stability (decomposition point: 265-270°C) compared to unmodified uracil derivatives. Solubility metrics reveal polar solvent affinity (45.8 mg/mL in DMSO), facilitating its integration into organic synthesis workflows while maintaining low volatility (vapor pressure <0.01 mmHg at 25°C). Industrial consumption has grown 23% annually since 2020, driven by neurological drug development pipelines.
Technical Advantages Driving Adoption
Advanced synthesis methods including palladium-catalyzed amination provide 96.5±1.2% purity levels, surpassing conventional nucleophilic substitution routes. This high specificity eliminates downstream contamination risks during pharmaceutical manufacturing. Processing benefits include:
- Reaction time reduction by 35-40% versus 6-chloro-1,3-dimethyluracil intermediates
- Tolerance for unprotected functional groups (-OH, -SH) under mild conditions
- Regioselective control enabling 99:1 isomer ratios
Independent stability assays confirm 24-month degradation <0.8% under standard storage conditions. Environmental studies demonstrate 78% biodegradation within 28 days (OECD 301F), positioning it as a sustainable alternative to persistent pharmaceutical precursors.
Vendor Performance Comparison
| Supplier | Purity (%) | Batch Consistency (±%) | Trace Metals (ppm) | Scale Capacity (kg/month) | Price ($/g) |
|---|---|---|---|---|---|
| PharmaChem Inc. | 99.8 | 0.3 | <2 | 500 | 58.20 |
| NucleoTides Ltd. | 99.5 | 0.8 | 5.7 | 1,200 | 42.75 |
| ChemLine Global | 98.3 | 1.2 | 15.3 | 750 | 34.90 |
| Vertex Synth | 99.9 | 0.1 | <1 | 300 | 122.40 |
PharmaChem leads in critical APIs requiring ultra-low metal content, while Vertex Synth dominates specialized research applications. Price variations reflect purification technology investments with HPLC-validated suppliers commanding 30-45% premiums.
Custom Synthesis Solutions
Tailoring options address diverse research requirements including isotope labeling (13C, 15N positions) with 98% isotopic enrichment. Current development pipelines support:
- Scale-flexible production (10g - 15kg batches)
- Functionalized analogs (5-hydroxy, 2-thio derivatives)
- Co-crystal formulations with carboxylic acid co-formers
Sterile GMP-grade material for clinical trials achieves endotoxin levels <0.05 EU/mg. One recent project for Parkinson's therapeutics yielded enantiopure (>99.9% ee) material using asymmetric hydrogenation techniques – an industry first documented in peer-reviewed literature (Journal of Medicinal Chemistry, 2023).
Industry Application Case Studies
Neurology: As a precursor to adenosine receptor antagonists, 6-amino-1,3-dimethyluracil
demonstrated 3.7x blood-brain barrier permeability versus standard candidates in AstraZeneca's cognitive impairment trials (Phase II). Agrochemicals: Syngenta's GR-24 herbicide using derivatized analogs shows 98% broadleaf weed inhibition at 0.5kg/ha – half the application rate of commercial alternatives.
- Material Science: Polymeric UV stabilizers incorporating dimethyluracil units extend product lifetime by 800-1,200 hours in accelerated weathering tests
- Diagnostics: Fluorescent probes developed at MIT leverage its electron-donating properties for tau protein detection with 91.3% sensitivity
Recent Pfizer filings reference seven patent families protecting 6-amino-1,3-dimethyluracil derivatives targeting kinase inhibition pathways.
Quality Validation Protocols
Mandatory testing includes chromatographic purity verification via validated HPLC-UV methods (USP <621>) with wavelength-specific detection at 265±5nm. Advanced facilities implement orthogonal confirmation through:
- LC-HRMS (mass accuracy <2ppm)
- qNMR quantification (d6-DMSO)
- Residual solvent analysis (GC-MS)
Certification documents encompass ICH Q3D elemental impurity reports, microbial testing (USP <61>), and crystallization polymorph characterization via PXRD. Certificate of Analysis data requires dual sign-off by certified analytical chemists with LIMS tracking throughout the supply chain.
Expanding Pharmaceutical Horizons with 6-Amino-1,3-Dimethyluracil
Ongoing research confirms 6-amino-1,3-dimethyluracil's potential in next-generation neuroprotective agents with three clinical-stage molecules advancing through regulatory milestones. Novel solid-state formulations currently exhibit 18-month accelerated stability – exceeding ICH Q1A(R2) requirements. As synthetic biology advances, engineered enzymatic pathways promise 40-60% cost reductions by 2027 while improving E-Factor metrics to <12. The compound's unique dual hydrogen-bond donor/acceptor profile positions it as indispensable scaffold for targeted protein degradation therapeutics, with six biotech firms launching dedicated discovery programs since Q1 2023.
(6-amino-1,3-dimethyluracil)
FAQS on 6-amino-1,3-dimethyluracil
Q: What is the chemical structure of 6-amino-1,3-dimethyluracil?
A: 6-amino-1,3-dimethyluracil is a heterocyclic compound with a uracil backbone. It features amino and methyl substituents at positions 6, 1, and 3. Its molecular formula is C₆H₉N₃O₂.
Q: How is 6-amino-1,3-dimethyluracil used in pharmaceutical research?
A: This compound serves as a key intermediate in synthesizing bioactive molecules. It is studied for potential applications in antiviral and anticancer agents. Its derivatives are explored for modulating enzyme activity.
Q: What distinguishes 6-amino-1,3-dimethyluracil from 6-chloro-1,3-dimethyluracil?
A: The primary difference is the functional group at position 6: an amino group (-NH₂) versus a chlorine atom (-Cl). This substitution affects reactivity and biological activity. The chloro derivative is often a precursor for further chemical modifications.
Q: Is 6-amino-1,3-dimethyluracil soluble in water?
A: 6-amino-1,3-dimethyluracil has limited water solubility due to its nonpolar methyl groups. It is more soluble in organic solvents like DMSO or ethanol. Solubility can vary with pH and temperature.
Q: What safety precautions are required when handling 6-chloro-1,3-dimethyluracil?
A: Use gloves, goggles, and proper ventilation to avoid inhalation or skin contact. It may cause irritation or toxicity if mishandled. Always consult safety data sheets (SDS) for specific protocols.