Chemical Structure and Composition

Benzyl [1-[4-[[(4-fluorobenzyl)amino]carbonyl]-5-hydroxy-1-methyl-6-oxo-1,6-dihydropyrimidin-2-yl]-1-methylethyl]carbamate (Aladdin SKU B193707) is a multi-functional small molecule built around a 5-hydroxy-1-methyl-6-oxo-1,6-dihydropyrimidine (dihydropyrimidinone) scaffold. Three distinct pharmacophoric elements are fused within the molecule:

• Dihydropyrimidinone core: The 1,6-dihydropyrimidin-2-one ring provides a planar, hydrogen-bond-rich heterocyclic framework widely encountered in bioactive natural products and pharmaceutical leads.
• C-5 hydroxyl group: The hydroxyl substituent at the 5-position of the ring enhances hydrogen-bonding capacity and can participate in metal coordination or intramolecular interactions relevant to enzyme active-site binding.
• 4-Fluorobenzyl amide: A 4-fluorobenzylamine-derived carboxamide at C-4 introduces a lipophilic, metabolically stable fluoroaromatic element frequently used in drug design to modulate pK_a, membrane permeability, and metabolic resistance.
• Cbz-protected quaternary amine: The C-2 substituent consists of a 2-aminopropan-2-yl (dimethylamino-type) group bearing a benzyloxycarbonyl (Cbz) carbamate, a standard amine-protecting strategy allowing selective deprotection under mild hydrogenolytic conditions.

This convergence of functional groups positions the compound as a versatile intermediate or probe in synthetic and medicinal chemistry workflows.

Physicochemical Properties and Handling

A thorough understanding of the physicochemical profile of this compound is essential for experimental design and safe laboratory handling.

Solubility and Storage

As a multi-ring heterocyclic compound bearing both polar (hydroxyl, amide, carbamate) and lipophilic (fluorobenzyl, benzyl) regions, the molecule is expected to display moderate polarity. Common research-grade solvents such as DMSO, DMF, and dichloromethane are likely suitable for stock solution preparation. Aqueous solubility may be limited due to the lipophilic aromatic substituents; a co-solvent strategy is recommended for biological assays. Stock solutions should be stored under inert atmosphere at low temperature (−20 °C recommended) to prevent hydrolysis of the carbamate linkage or oxidation of the enol/hydroxyl moiety.

Stability Considerations

The Cbz carbamate is stable under acidic and basic aqueous conditions at ambient temperature but is labile to catalytic hydrogenolysis (e.g., Pd/C, H₂ or ammonium formate). The 5-hydroxy-dihydropyrimidinone may exhibit tautomerism between the hydroxyl and carbonyl (keto–enol) forms; NMR characterization in DMSO-d₆ is advisable to confirm tautomeric state in solution. Researchers should avoid prolonged exposure to strong acids or bases, which may hydrolyze the amide or carbamate functionalities.

Analytical Characterization

Identity confirmation should include ¹H NMR, ¹³C NMR, HRMS, and HPLC purity assessment. The ¹⁹F NMR signal from the 4-fluorobenzyl group provides a convenient analytical handle for tracking the compound through synthetic sequences.

Research and Synthetic Applications

The structural features of this compound make it relevant across several research domains:

Medicinal Chemistry and Drug Discovery

The dihydropyrimidinone (DHPM) scaffold is a privileged heterocycle in medicinal chemistry, associated with a wide range of biological activities including antihypertensive, antiviral, antibacterial, and antitumor properties in related compound series. The present molecule, with its elaborated C-2 and C-4 substituents, may serve as a lead compound, an advanced intermediate for SAR (structure–activity relationship) studies, or a reference standard in assay development. The 4-fluorobenzyl group is particularly notable because fluorine substitution on aromatic rings is a widely used medicinal chemistry strategy to improve metabolic stability and fine-tune lipophilicity.

Synthetic Intermediates and Cbz Deprotection

As a Cbz-protected amine at a quaternary carbon center, this compound is a useful intermediate en route to free-amine analogs. The Cbz group can be removed by palladium-catalyzed hydrogenolysis under standard conditions, liberating the primary amine for further functionalization (e.g., acylation, reductive amination, coupling reactions). This makes it valuable in multi-step synthesis programs targeting related pyrimidinone amines.

Chemical Biology Probes

Compounds integrating a fluorobenzyl moiety and a dihydropyrimidinone can be considered as candidate scaffolds for developing labeled probes or fragment-based screening libraries. Researchers working on enzyme inhibition or protein–ligand interaction studies may find this compound useful as a fragment hit or optimization starting point.

Ordering, Packaging, and Quality Assurance

Aladdin Scientific supplies Benzyl [1-[4-[[(4-fluorobenzyl)amino]carbonyl]-5-hydroxy-1-methyl-6-oxo-1,6-dihydropyrimidin-2-yl]-1-methylethyl]carbamate under catalog number B193707. Researchers should consult the current product page for up-to-date information on available pack sizes, pricing, purity specifications, and Certificate of Analysis (CoA) documentation.

Each lot is quality-controlled and shipped with a CoA detailing purity (typically assessed by HPLC), appearance, and spectroscopic data where available. For sensitive applications such as biological screening or reference standard use, customers are advised to request the CoA before use and to verify the compound identity by independent NMR or MS analysis upon receipt.

For bulk quantities, custom synthesis inquiries, or special purity grades, contact Aladdin Scientific's technical sales team directly. Standard shipping conditions for this type of compound typically involve ambient or cold-chain packaging; refer to the product SDS (Safety Data Sheet) for proper transport and storage requirements.