Chemical Structure and Physicochemical Properties

1-(5-Bromopyrimidin-2-yl)-3-piperidinol (Aladdin SKU B195798) combines two pharmacologically important heterocyclic motifs: a pyrimidine ring bearing a bromine substituent at the 5-position and a piperidine ring carrying a hydroxyl group at the 3-position. The nitrogen atom at position 1 of the piperidine is directly bonded to carbon 2 of the pyrimidine, forming a C–N bond that connects the two rings.

The molecular formula is C₉H₁₂BrN₃O, giving a calculated molecular weight of approximately 258.12 g/mol. The compound possesses a chiral center at the 3-position of the piperidine ring; the racemic mixture is typically supplied unless a specific enantiomer is stated. Key functional groups include an electrophilic aryl C–Br bond (reactive in metal-catalyzed cross-coupling), a nucleophilic piperidine nitrogen embedded in the ring, and a free secondary hydroxyl group that can participate in further functionalization such as esterification, etherification, or oxidation to a ketone.

The presence of three nitrogen atoms and one oxygen atom confers significant hydrogen-bonding capacity, which generally enhances aqueous solubility relative to purely carbocyclic analogues. Predicted physicochemical parameters (logP, pKa, melting point) should be verified against the Certificate of Analysis (CoA) and Safety Data Sheet (SDS) supplied with each lot.

Synthetic Utility and Reactivity

The aryl bromide moiety on the pyrimidine ring makes 1-(5-Bromopyrimidin-2-yl)-3-piperidinol a highly versatile electrophilic partner in transition-metal-catalyzed reactions. Palladium-catalyzed processes — including Suzuki–Miyaura (boronic acid/ester coupling), Buchwald–Hartwig (amination), Negishi (organozinc), and Sonogashira (terminal alkyne) couplings — can selectively functionalize the C5 position of the pyrimidine to introduce diverse aryl, heteroaryl, amino, or alkynyl substituents.

Nucleophilic aromatic substitution (SNAr) at C2 of the pyrimidine is generally less applicable given that the piperidine nitrogen is already installed at that position; however, the electronic character of the pyrimidine ring may facilitate further modifications under appropriate conditions. The secondary hydroxyl at the 3-position of the piperidine provides an orthogonal handle: it can be protected as a silyl ether, converted to a leaving group (mesylate or tosylate) for SN2 displacement, oxidized to the corresponding ketone using Swern or Dess–Martin conditions, or acylated to introduce ester or carbamate motifs.

This bifunctional reactivity profile makes the compound particularly attractive for the parallel synthesis of compound libraries in drug-discovery settings, where simultaneous diversification at both the C5-bromine and the C3-hydroxyl sites can rapidly generate structural diversity.

Handling, Storage, and Safety Guidelines

Personal Protective Equipment (PPE): When handling 1-(5-Bromopyrimidin-2-yl)-3-piperidinol, wear appropriate chemical-resistant gloves (nitrile recommended), laboratory coat, and eye protection (safety goggles). Work in a fume hood whenever possible to minimize inhalation of dust or aerosols.

Storage: Store the compound in a tightly sealed container in a cool (typically 2–8 °C or room temperature as specified on the CoA), dry, well-ventilated location, protected from light and moisture. Prolonged exposure to air and humidity may lead to gradual degradation; desiccants are recommended for long-term storage. Keep away from incompatible materials including strong oxidizing agents, strong bases, and reactive metals.

Disposal: Dispose of waste material in accordance with local, regional, and national regulations for halogenated organic compounds. Do not dispose of via drain or general waste streams without authorization.

First Aid: In case of skin or eye contact, flush immediately with copious amounts of water for at least 15 minutes and seek medical advice. For inhalation, move to fresh air. Consult the full SDS (available from Aladdin Scientific) for comprehensive hazard information, GHS classifications, and emergency procedures specific to each lot.

Note: The specific GHS hazard categories and H/P statements should be confirmed from the product SDS, as these are lot-dependent and subject to regulatory classification updates.

Quality, Purity, and Analytical Characterization

Aladdin Scientific supplies 1-(5-Bromopyrimidin-2-yl)-3-piperidinol (B195798) at research-reagent grade. Researchers should consult the Certificate of Analysis (CoA) for each specific lot to verify the guaranteed purity (typically ≥95% by HPLC or NMR for research-grade materials), appearance, and any analytical data provided.

Recommended analytical methods for identity and purity confirmation:

• ¹H and ¹³C NMR Spectroscopy: The most definitive method for structural confirmation. Characteristic signals include aromatic protons on the pyrimidine ring (typically appearing as singlets in the 8–9 ppm region), aliphatic protons of the piperidine ring (1.5–4.0 ppm), and the hydroxyl-bearing methine proton (3.5–4.0 ppm). The stereochemistry at C3 of the piperidine may manifest as diastereotopic proton patterns.
• HPLC: Reverse-phase HPLC (C18 column, UV detection at 254 nm or compound-specific wavelength) provides quantitative purity assessment.
• LC-MS or HRMS: Confirms molecular weight and molecular formula; the characteristic isotope pattern of bromine (approximately 1:1 ratio of ⁷⁹Br:⁸¹Br) is a reliable identity marker in mass spectra.
• Melting Point: Useful as a physical identity check; reference value should be obtained from the CoA.

If the compound is to be used in sensitive biological assays, additional purity checks (e.g., Karl Fischer water content, residual solvent analysis by ¹H NMR or GC-headspace) are advisable.

Applications in Drug Discovery and Medicinal Chemistry

The 2-aminopyrimidine fragment embedded in 1-(5-Bromopyrimidin-2-yl)-3-piperidinol is a privileged structural motif found in numerous kinase inhibitors, antiviral agents, and other bioactive molecules. Pyrimidines are known to form productive hydrogen-bonding interactions with hinge regions of kinase ATP-binding sites, making pyrimidine-containing scaffolds a cornerstone of kinase inhibitor design.

The 3-hydroxypiperidine moiety contributes favorable ADME (absorption, distribution, metabolism, excretion) properties: piperidines are a frequently encountered ring system in approved drugs due to their metabolic stability, conformational rigidity, and ability to modulate physicochemical parameters such as basicity and solubility. The hydroxyl group can be exploited to tune polarity, introduce hydrogen-bond donor/acceptor character, or serve as a synthetic handle for prodrug strategies.

Together, the bromopyrimidine and hydroxypiperidine elements position B195798 as a useful intermediate for the preparation of:

• Kinase inhibitor candidates via Suzuki coupling at C5 of the pyrimidine to install biaryl pharmacophores
• Fragment-based drug discovery (FBDD) starting points, given the low molecular weight and drug-like properties of the scaffold
• PROteolysis TArgeting Chimeras (PROTACs) and bifunctional molecules, where orthogonal reactive handles are required
• Agrochemical and material-science applications requiring halogenated nitrogen-heterocycle intermediates

Disclaimer: No specific biological activity data for B195798 itself are claimed; intended use is as a synthetic building block. Researchers should conduct independent biological evaluation.