4,6-Dimethylpyrimidin-5-amine: Properties, Handling & Lab Use
4,6-Dimethylpyrimidin-5-amine: Properties, Handling & Lab Use
4,6-Dimethylpyrimidin-5-amine is a substituted aminopyrimidine building block widely employed in medicinal chemistry, heterocyclic synthesis, and the preparation of biologically active compounds.
- CAS Number
- 5407-87-4
- Molecular Formula
- C6H9N3
- Molecular Weight
- 123.16 g/mol
- Core Structure
- Pyrimidine ring with methyl groups at positions 4 and 6, and a primary amine at position 5
- Appearance
- Typically a white to off-white crystalline solid (verify with CoA)
- Recommended Storage
- Cool, dry, well-ventilated area; sealed container away from moisture and light
- SKU
- D195764
Chemical Identity and Structure
4,6-Dimethylpyrimidin-5-amine (CAS 5407-87-4) belongs to the aminopyrimidine class of heterocyclic compounds. Its molecular formula is C6H9N3 with a molecular weight of approximately 123.16 g/mol. The molecule features a six-membered pyrimidine ring bearing methyl substituents at the 4- and 6-positions and a primary amino group (–NH2) at the 5-position.
This substitution pattern creates a symmetric, electron-rich aromatic system. The amino group at C-5 is flanked by two electron-donating methyl groups, which modulates the basicity of the ring nitrogens and the nucleophilicity of the exocyclic amine, making this compound a versatile intermediate for further functionalization such as acylation, condensation, and transition-metal-catalyzed cross-coupling reactions.
Physicochemical Properties and Purity Specifications
4,6-Dimethylpyrimidin-5-amine is typically obtained as a white to off-white crystalline solid. Key physicochemical attributes relevant to laboratory use include:
- Solubility: The compound is expected to show moderate solubility in polar protic solvents such as methanol, ethanol, and water (aided by its basic amine), and good solubility in polar aprotic solvents such as DMSO and DMF. Solubility in non-polar solvents is expected to be limited.
- Basicity: As an aminopyrimidine, the compound possesses basic character derived from both the ring nitrogens and the exocyclic amine. This renders it susceptible to salt formation with mineral and organic acids.
- Stability: The compound is expected to be stable under normal laboratory conditions when stored appropriately. Prolonged exposure to moisture, strong oxidising agents, or strong acids should be avoided.
Purity and exact physicochemical data (melting point, specific NMR, HPLC purity) should always be confirmed against the Certificate of Analysis (CoA) supplied with each lot of SKU D195764.
Research Applications
The 5-aminopyrimidine motif is a privileged scaffold in drug discovery and chemical biology. 4,6-Dimethylpyrimidin-5-amine serves as a useful building block in several research contexts:
- Medicinal Chemistry: Aminopyrimidines are core structural elements in kinase inhibitors, antiviral agents, and antimicrobial compounds. The 4,6-dimethyl substitution provides steric and electronic tuning around the amine, enabling structure–activity relationship (SAR) exploration.
- Heterocyclic Synthesis: The primary amine at C-5 can participate in condensation reactions with carbonyl-containing partners (aldehydes, ketones, acid chlorides, anhydrides) to yield imines, amides, and fused ring systems, including pyrimido-fused heterocycles.
- Agrochemical Research: Pyrimidine-based amines are found in herbicides and fungicides; this compound may serve as a structural analogue or starting material in agrochemical lead optimisation programmes.
- Ligand Design: The combination of pyrimidine ring nitrogens and the exocyclic amine provides multiple coordination sites, making this compound potentially useful as a ligand precursor in coordination chemistry and catalysis research.
Safe Handling, Storage, and Disposal
Although specific GHS hazard classification data for 4,6-Dimethylpyrimidin-5-amine should be confirmed via the Safety Data Sheet (SDS) supplied with SKU D195764, general best-practice guidelines for handling aminopyrimidine research reagents apply:
- Personal Protective Equipment (PPE): Wear appropriate gloves (nitrile recommended), safety goggles, and a laboratory coat. Work in a well-ventilated fume hood when weighing or handling powders to minimise inhalation exposure.
- Storage: Store in a tightly sealed container in a cool (2–25 °C recommended; confirm on CoA/SDS), dry, well-ventilated area, away from direct light, moisture, strong oxidising agents, and strong acids. Keep container closed when not in use.
- Stability: Under correct storage conditions the compound is expected to be stable; re-verify purity by analytical methods (TLC, NMR, HPLC) if the reagent has been stored for an extended period or if discolouration is observed.
- Disposal: Dispose of waste material in accordance with local, regional, and national regulations for chemical waste. Do not dispose of via municipal sewage systems. Consult your institution's Environmental Health and Safety (EHS) office for approved disposal routes.
Always consult the current SDS before first use.
Frequently asked questions
What is the recommended solvent for dissolving 4,6-Dimethylpyrimidin-5-amine in solution-phase reactions?
DMSO and DMF are generally excellent solvents for this aminopyrimidine due to its polar functionality and moderate molecular weight. Polar protic solvents such as ethanol or methanol are also suitable. For aqueous applications, dilute acid solutions may improve solubility by protonating the basic amine. Always perform a small-scale solubility test before preparing bulk stock solutions.
How should I store 4,6-Dimethylpyrimidin-5-amine to maintain long-term stability?
Store the compound in a tightly sealed container under cool, dry, and dark conditions. Exposure to moisture can promote degradation of the primary amine. Always confirm the specific storage temperature and shelf-life on the Certificate of Analysis (CoA) and Safety Data Sheet (SDS) provided with SKU D195764. For long-term storage, consider using desiccants and minimising freeze-thaw cycles if stored at low temperature.
Is 4,6-Dimethylpyrimidin-5-amine suitable as a direct kinase inhibitor or is it purely a synthetic building block?
At the molecular weight of 123.16 g/mol, this compound is too small to function as a standalone kinase inhibitor; it is primarily valuable as a synthetic building block or fragment for constructing more complex biologically active molecules. Researchers engaged in fragment-based drug discovery (FBDD) may also evaluate such fragments as starting points, but further elaboration of the scaffold is typically required to achieve meaningful biological activity.
What analytical methods are appropriate for confirming the identity and purity of this compound?
Standard characterisation methods include 1H and 13C NMR spectroscopy for structural identity, HPLC with UV detection for purity determination, and LC-MS for molecular weight confirmation. Melting point determination can serve as a rapid initial purity check. Always compare results against the CoA provided by Aladdin Scientific for SKU D195764.
References
- Joule, J. A.; Mills, K. Heterocyclic Chemistry, 5th ed.; Wiley-Blackwell: Oxford, 2010. (General reference for pyrimidine chemistry)
- Aladdin Scientific Certificate of Analysis, SKU D195764, 4,6-Dimethylpyrimidin-5-amine. (Consult current lot CoA for purity, melting point, and NMR data.)
- Aladdin Scientific Safety Data Sheet, SKU D195764, 4,6-Dimethylpyrimidin-5-amine. (Consult for GHS hazard classification, first-aid measures, and disposal guidance.)
Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
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