Methyl 2-Phenylpyrimidine-5-Carboxylate: Properties & Uses
Methyl 2-Phenylpyrimidine-5-Carboxylate: Properties & Uses
Methyl 2-phenylpyrimidine-5-carboxylate is a versatile arylpyrimidine ester building block that serves as a key intermediate in medicinal chemistry programs and heterocyclic synthesis workflows.
- Chemical Name
- Methyl 2-phenylpyrimidine-5-carboxylate
- SKU
- P725699
- Molecular Formula
- C12H10N2O2
- Molecular Weight
- 214.22 g/mol
- Core Structure
- Pyrimidine ring bearing a 2-phenyl substituent and a methyl ester at position 5
- Primary Application
- Synthetic building block in medicinal chemistry and heterocyclic chemistry
- Supplier
- Aladdin Scientific
Chemical Structure and Physicochemical Properties
Methyl 2-phenylpyrimidine-5-carboxylate (CAS registry; molecular formula C12H10N2O2; MW 214.22 g/mol) belongs to the class of 2-arylpyrimidine-5-carboxylate esters. Its structure consists of an electron-deficient pyrimidine ring substituted at the 2-position with a phenyl group and at the 5-position with a methoxycarbonyl (methyl ester) group.
The electron-withdrawing nature of both the ring nitrogen atoms and the ester functionality renders the pyrimidine ring significantly electron-poor, making it susceptible to nucleophilic aromatic substitution and facilitating coordination to metal catalysts in cross-coupling reactions. The 2-phenyl group introduces additional conjugation, influencing UV absorption and crystalline packing. The compound is typically encountered as a white to off-white crystalline solid with moderate solubility in common organic solvents such as dichloromethane, ethyl acetate, and dimethyl sulfoxide, and limited solubility in water.
Note: Specific melting point, exact CAS number, and solubility data should be verified against the certificate of analysis (CoA) provided with SKU P725699.
Synthesis and Synthetic Utility
2-Arylpyrimidine-5-carboxylate esters such as Methyl 2-phenylpyrimidine-5-carboxylate are commonly accessed via condensation strategies, including the reaction of appropriate amidines with 1,3-dicarbonyl equivalents, or through palladium-catalyzed cross-coupling of halopyrimidine precursors with arylboronic acids (Suzuki–Miyaura coupling). The methyl ester at position 5 serves as a versatile handle for further elaboration.
In synthetic workflows, the ester group can be hydrolyzed to the corresponding carboxylic acid, reduced to the alcohol, converted to an amide via aminolysis, or utilized in Knoevenagel-type condensations. The 2-phenyl group can be further functionalized if the phenyl ring bears additional reactive substituents. This multifunctionality makes SKU P725699 a valuable intermediate for library synthesis in drug discovery campaigns.
The electron-deficient pyrimidine core is also well-suited for SNAr reactions when halogen substituents are present on analogous substrates, providing routes to diverse 2,4,5-trisubstituted pyrimidines relevant to bioactive compound synthesis.
Applications in Medicinal Chemistry
The pyrimidine scaffold is one of the most prevalent nitrogen-containing heterocycles in approved pharmaceuticals and drug candidates. Compounds bearing the 2-arylpyrimidine motif have been identified as kinase inhibitors, antifungal agents, antiviral compounds, and modulators of various biological targets. Methyl 2-phenylpyrimidine-5-carboxylate serves as a direct precursor or structural analogue in the preparation of such bioactive molecules.
Researchers engaged in structure–activity relationship (SAR) studies frequently employ this compound to explore how substituents on the pyrimidine ring and the pendant phenyl group modulate target binding affinity, selectivity, and pharmacokinetic properties. The methyl ester at position 5 can be converted to diverse functional groups (acids, amides, aldehydes, alcohols) to probe interactions within the binding site of protein targets.
Furthermore, the 2-phenylpyrimidine unit is recognized as a metal-chelating motif in coordination chemistry, with applications in the design of luminescent materials and organometallic catalysts, broadening the utility of this building block beyond traditional pharmaceutical research.
Handling, Storage, and Safety Considerations
As with all fine chemical reagents, Methyl 2-phenylpyrimidine-5-carboxylate should be handled with standard laboratory precautions. Personnel should wear appropriate personal protective equipment (PPE) including nitrile gloves, safety glasses, and a laboratory coat. Operations generating dust or aerosols should be conducted in a well-ventilated area or fume hood.
The compound should be stored in a tightly sealed container, away from heat, moisture, and incompatible materials such as strong oxidizers and strong bases. Storage under inert atmosphere (nitrogen or argon) is recommended to maintain long-term stability. Recommended storage temperature is typically ambient or at 2–8 °C; please refer to the product label and CoA for the specific recommendation for SKU P725699.
Disposal must comply with local, regional, and national regulations governing chemical waste. Consult the Safety Data Sheet (SDS) available from Aladdin Scientific for complete hazard classification, first-aid measures, and disposal guidance specific to this compound.
Frequently asked questions
What is Methyl 2-phenylpyrimidine-5-carboxylate used for in research?
Methyl 2-phenylpyrimidine-5-carboxylate is primarily used as a synthetic building block in medicinal chemistry and heterocyclic synthesis. Its methyl ester handle enables transformation into a wide range of functional groups, and the 2-arylpyrimidine scaffold is prevalent in kinase inhibitor and antifungal drug discovery programs.
How should Methyl 2-phenylpyrimidine-5-carboxylate (P725699) be stored?
The compound should be stored in a tightly sealed container under inert atmosphere, away from moisture, heat, and strong oxidizing agents. For specific temperature and shelf-life recommendations, always refer to the certificate of analysis (CoA) and product label supplied with SKU P725699 by Aladdin Scientific.
Can the methyl ester group of this compound be readily functionalized?
Yes. The methyl ester at position 5 of the pyrimidine ring is a versatile synthetic handle. It can be hydrolyzed to the carboxylic acid under basic or acidic conditions, reduced to the primary alcohol, converted to amides via aminolysis, or employed in condensation reactions, making this compound highly adaptable for library synthesis and SAR studies.
Is Methyl 2-phenylpyrimidine-5-carboxylate soluble in common laboratory solvents?
The compound is generally soluble in polar aprotic solvents such as DMSO and DMF, as well as chlorinated solvents like dichloromethane and ethyl acetate. Its solubility in water is expected to be low due to the hydrophobic pyrimidine-phenyl core. Always verify solubility data experimentally or consult the SDS and CoA for SKU P725699.
References
- Joule, J. A.; Mills, K. Heterocyclic Chemistry, 5th ed.; Wiley-Blackwell: Oxford, 2010. General reference for pyrimidine chemistry and reactivity.
- Clayden, J.; Greeves, N.; Warren, S. Organic Chemistry, 2nd ed.; Oxford University Press: Oxford, 2012. General reference for ester reactivity and functional group interconversions.
- Miyaura, N.; Suzuki, A. Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds. Chem. Rev. 1995, 95, 2457–2483. Foundational reference for Suzuki–Miyaura coupling used in arylpyrimidine synthesis. doi:10.1021/cr00039a007
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