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Comprehensive Overview of 4-Amino-2-methoxypyrimidine-5-carbaldehyde (CAS No. 26664-09-5): Properties, Applications, and Industry Insights

4-Amino-2-methoxypyrimidine-5-carbaldehyde (CAS No. 26664-09-5) is a specialized heterocyclic compound that has garnered significant attention in pharmaceutical and agrochemical research due to its unique structural features. This pyrimidine derivative serves as a versatile building block in organic synthesis, particularly in the development of nucleoside analogs and enzyme inhibitors. The presence of both amino and aldehyde functional groups on the methoxypyrimidine scaffold enables diverse chemical modifications, making it valuable for drug discovery pipelines targeting viral infections and metabolic disorders.

Recent studies highlight the compound's role in designing kinase inhibitors, a hot topic in oncology research. As interest grows in personalized medicine, researchers are exploring how 4-Amino-2-methoxypyrimidine-5-carbaldehyde derivatives can be tailored to modulate specific biological pathways. The methoxy group at the 2-position enhances metabolic stability—a critical factor addressed in many "drug-likeness" optimization queries from medicinal chemists. Computational chemistry approaches (frequently searched in AI-driven drug design) predict favorable binding affinities when this scaffold is incorporated into larger pharmacophores.

From a synthetic chemistry perspective, the aldehyde functionality at the 5-position allows for convenient condensation reactions, answering frequent search queries about "pyrimidine aldehyde applications in click chemistry." The compound's molecular weight (153.14 g/mol) and moderate polarity make it suitable for various formulation strategies—a concern often raised in pharmaceutical development forums. Analytical data shows characteristic NMR peaks at δ 9.85 ppm (aldehyde proton) and δ 6.15 ppm (pyrimidine H-6), which serve as important identification markers for quality control laboratories.

Environmental scientists have investigated the biodegradation pathways of such amino-methoxypyrimidine compounds in response to growing regulatory demands for "green chemistry" solutions. The compound demonstrates moderate aqueous solubility (approximately 2.1 g/L at 25°C), influencing its environmental fate—a parameter increasingly searched in ecological risk assessment databases. Thermal analysis reveals stability up to 180°C, making it compatible with common industrial processing conditions.

In material science applications, the planar pyrimidine core of 4-Amino-2-methoxypyrimidine-5-carbaldehyde enables π-stacking interactions that interest researchers developing organic semiconductors. This aligns with trending searches about "small molecule electronics" and "bio-inspired materials." The compound's ability to form Schiff bases (a frequently studied reaction in supramolecular chemistry) further expands its utility in creating functionalized surfaces for biosensors.

Quality specifications for CAS No. 26664-09-5 typically require ≥98% purity by HPLC, with particular attention to residual solvent levels—a compliance aspect heavily emphasized in current Good Manufacturing Practice (cGMP) discussions. Storage recommendations suggest protection from light at 2-8°C under inert atmosphere, addressing common compound stability questions from inventory managers. The material safety data sheet provides standard handling precautions comparable to other research chemicals in its class.

Market analysts note growing demand for this pyrimidine aldehyde precursor, particularly from contract research organizations engaged in fragment-based drug discovery. Patent landscape reviews show increasing citations of 4-Amino-2-methoxypyrimidine-5-carbaldehyde in applications related to "allosteric modulator development"—a trending topic in receptor pharmacology. Custom synthesis inquiries often focus on isotopic labeling (13C/15N) versions for metabolic studies, reflecting the compound's expanding role in mechanistic research.

Academic laboratories value this compound for teaching advanced heterocyclic chemistry concepts, with particular emphasis on its use in demonstrating regioselective functionalization—answering common educational queries about "pyrimidine reactivity patterns." The crystalline form (monoclinic system) has been characterized by X-ray diffraction, providing concrete structural data for computational modeling validation—a crucial step in modern structure-activity relationship studies.

Emerging applications in bioconjugation chemistry leverage the compound's dual reactivity, addressing frequent search terms about "orthogonal protection strategies" in peptide modification. Process chemists have developed scalable routes to 4-Amino-2-methoxypyrimidine-5-carbaldehyde using continuous flow systems—an area gaining traction in industrial optimization forums. The compound's balanced lipophilicity (calculated logP ~0.7) makes it particularly interesting for blood-brain barrier penetration studies, a persistent challenge in CNS drug development.

Recent innovations include using this aminoaldehyde derivative as a template for creating fluorescence probes—responding to growing interest in "small molecule sensors" for biological imaging. The electron-withdrawing nature of the methoxypyrimidine ring influences its UV-Vis spectrum (λmax ~285 nm in methanol), a property useful for analytical method development. Regulatory documentation indicates compliance with major pharmacopeia standards when manufactured under controlled conditions.

Technical discussions frequently address the compound's stability in various pH conditions—a practical consideration for formulation scientists searching "pyrimidine aldehyde compatibility." The 4-Amino-2-methoxypyrimidine-5-carbaldehyde scaffold shows promise in metal-organic framework (MOF) construction, tapping into nanotechnology research trends. Comparative studies with similar pyrimidine carbaldehydes reveal distinct reactivity patterns that inform rational design strategies in medicinal chemistry programs.

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• 7356-61-8(ethyl 4-amino-2-methoxypyrimidine-5-carboxylate)
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