Chemical Identity and Physical Properties

Methyl 2-phenylpyrimidine-5-carboxylate (CAS number subject to verification; SKU P725699) is an aromatic heterocyclic compound featuring a pyrimidine ring bearing a phenyl substituent at the 2-position and a methyl ester group at the 5-position. Its molecular formula is C₁₂H₁₀N₂O₂ with a molecular weight of approximately 214.22 g/mol.

The compound is typically a white to off-white crystalline solid at room temperature. Key physical characteristics include moderate solubility in common polar organic solvents such as dimethyl sulfoxide (DMSO), dimethylformamide (DMF), ethyl acetate, and dichloromethane, with limited solubility in water. The ester functionality and the electron-deficient pyrimidine ring contribute to its reactivity as a synthetic building block, enabling diverse downstream transformations including hydrolysis, amide coupling, cross-coupling reactions, and nucleophilic additions.

Note: Specific melting point, boiling point, and spectral data (NMR, HPLC purity) should be confirmed against the certificate of analysis (CoA) provided by Aladdin Scientific for lot P725699.

Storage, Handling, and Safety Guidelines

Proper storage and handling of Methyl 2-phenylpyrimidine-5-carboxylate are essential to maintain reagent integrity and ensure laboratory safety.

Storage Conditions: Store the compound in a tightly sealed container in a cool (15–25 °C), dry location away from direct light, heat sources, and moisture. Prolonged exposure to humidity may promote ester hydrolysis and reduce purity. For long-term storage, consider refrigeration at 2–8 °C under an inert atmosphere (nitrogen or argon).

Handling Precautions: Use appropriate personal protective equipment (PPE) including nitrile gloves, safety glasses, and a laboratory coat when handling this compound. Work in a well-ventilated area or fume hood to minimize inhalation exposure to dust or aerosols. Avoid contact with skin, eyes, and mucous membranes.

Compatibility: Keep away from strong oxidizing agents, strong bases, and strong acids that could hydrolyze the ester group or degrade the heterocyclic ring system.

Disposal: Dispose of waste material in accordance with local, national, and institutional regulations for organic chemical waste. Refer to the Safety Data Sheet (SDS) for complete hazard information before use.

Review flag: Specific GHS hazard classifications and pictograms for this compound should be confirmed from the official SDS for P725699 prior to publication.

Recommended Laboratory Protocols

Methyl 2-phenylpyrimidine-5-carboxylate serves as a versatile intermediate in synthetic chemistry. The following protocols outline common preparative and transformative applications.

1. Solution Preparation: To prepare a stock solution, weigh the desired quantity of compound using an analytical balance in a dry environment. Dissolve in anhydrous DMSO or DMF at concentrations of 0.1–1.0 M, depending on the downstream reaction requirements. For reactions sensitive to protic solvents, ensure the solvent is freshly dried or purchased as anhydrous grade.

2. Saponification (Ester Hydrolysis) to the Carboxylic Acid: The methyl ester can be converted to the corresponding carboxylic acid (2-phenylpyrimidine-5-carboxylic acid) using aqueous base (e.g., LiOH or NaOH, 1–4 equivalents) in a THF/MeOH/H₂O solvent system at room temperature to 60 °C. Monitor reaction progress by TLC or LC-MS. Acidify the aqueous workup to pH 2–3 with dilute HCl to precipitate or extract the product.

3. Amide Bond Formation: The carboxylate (obtained after hydrolysis) or the activated ester can be coupled to primary or secondary amines using standard peptide coupling reagents (e.g., HATU, EDC/HOBt) in DMF with a non-nucleophilic base (e.g., DIPEA, 2–3 equivalents) to generate pyrimidine-5-carboxamide derivatives, which are of interest in medicinal chemistry.

4. Palladium-Catalyzed Cross-Coupling: Although the 2-phenyl group is pre-installed, the pyrimidine ring system can participate in directed C–H functionalization or further diversification at other positions under appropriate Pd-catalyzed or directed metalation conditions.

All protocols should be optimized for the specific reaction scale, substrate, and institutional safety guidelines. Yields and conditions cited here are indicative and should be experimentally verified.

Applications in Research and Drug Discovery

The 2-phenylpyrimidine-5-carboxylate scaffold is a privileged structural motif in medicinal chemistry and chemical biology. Pyrimidine rings are bioisosteres of pyridine and benzene and are found in numerous bioactive natural products and approved pharmaceuticals.

Medicinal Chemistry: The 2-arylpyrimidine-5-carboxylate framework serves as a building block for kinase inhibitor synthesis, anti-infective agents, and other therapeutic targets. The ester group provides a handle for diversification via hydrolysis to the acid, conversion to amides or other functional groups, enabling rapid analogue synthesis in structure–activity relationship (SAR) studies.

Agrochemical Research: Pyrimidine-containing compounds are well-represented in herbicide, fungicide, and insecticide chemistry. Methyl 2-phenylpyrimidine-5-carboxylate may serve as a precursor in the synthesis of pyrimidine-based agrochemical candidates.

Material Science: Functionalized pyrimidines have been explored in organic semiconductors and coordination polymer chemistry, where nitrogen-rich heterocycles act as ligands or charge-transport units.

Review flag: Specific literature references citing this exact compound in biological or agrochemical applications were not available in the source material. Claims should be validated with primary literature before publication.

Ordering, Specifications, and Quality Assurance

Methyl 2-phenylpyrimidine-5-carboxylate is available from Aladdin Scientific under SKU P725699. Researchers and procurement teams should note the following when placing orders:

Purity and Specifications: Aladdin Scientific provides a certificate of analysis (CoA) with each lot, confirming identity (NMR or HPLC), purity grade, and lot-specific data. Researchers are advised to request the CoA prior to use in critical assays.

Available Pack Sizes: Please consult the Aladdin Scientific product page for current pack sizes and pricing. Pack sizes typically range from milligram to multi-gram quantities to accommodate screening through scale-up needs.

Ordering Process: Orders can be placed through the Aladdin Scientific online platform. For bulk or custom quantity inquiries, contact the sales or technical support team directly.

Returns and Quality Issues: If product quality does not meet specifications as stated in the CoA, contact Aladdin Scientific customer service in accordance with the return and refund policy. Provide the lot number and CoA data when reporting quality concerns.

Shipping and Storage on Receipt: Upon receipt, inspect the package for integrity. If the compound is received at ambient temperature, re-seal promptly and transfer to appropriate storage conditions as described in the storage section above.