Chemical Identity and Structure

6-Chloro-2-(pyridin-2-yl)pyrimidin-4-amine (SKU: C189325) belongs to the class of 2-arylpyrimidine derivatives. Its molecular formula is C₉H₇ClN₄, giving a molecular weight of approximately 206.63 g/mol. The compound comprises a pyrimidine core substituted at position 2 with a pyridin-2-yl group and bearing both a chloro group at position 6 and an amino group at position 4. This combination of substituents creates a highly versatile scaffold for downstream chemical elaboration.

The presence of multiple nitrogen atoms confers hydrogen-bond donor and acceptor capacity, which is advantageous for engaging biological targets. The C-6 chlorine renders the ring electron-deficient and therefore activated toward nucleophilic aromatic substitution (SNAr) reactions. The amino group at C-4 can participate in acylation, sulfonylation, or further condensation reactions. Researchers should consult the official product datasheet and Certificate of Analysis (CoA) available from Aladdin Scientific for confirmed purity, exact CAS number, and physical constants.

Storage, Handling, and Safety Guidelines

Storage: Store 6-Chloro-2-(pyridin-2-yl)pyrimidin-4-amine under cool, dry, and dark conditions in a tightly sealed container. Specific temperature requirements (e.g., room temperature, 2–8 °C, or −20 °C) should be confirmed on the product label and CoA supplied with each lot. Improper storage may lead to degradation or reduced purity over time.

Handling: Always handle this compound in a well-ventilated fume hood wearing appropriate personal protective equipment (PPE), including nitrile gloves, a laboratory coat, and safety glasses. Minimize exposure to moisture and air if the compound is hygroscopic (verify with CoA). Weigh quantities in a closed environment to avoid dust inhalation.

Safety: Consult the Safety Data Sheet (SDS) for this product before use. In the absence of published toxicological data, treat all halogenated heterocyclic amines as potentially harmful. Avoid ingestion, skin contact, and inhalation. Dispose of waste material in accordance with local and institutional regulations for hazardous chemical waste.

Stability: The C–Cl bond is stable under ambient conditions but may hydrolyze slowly under strongly acidic or basic aqueous conditions. Store solutions in anhydrous solvents (e.g., DMSO, DMF, acetonitrile) when prepared in advance, and keep refrigerated.

Synthetic Applications and Reaction Protocols

Nucleophilic Aromatic Substitution (SNAr): The C-6 chloro group is the primary reactive handle. Under mild to moderate heating (60–120 °C, verify optimal conditions for each substrate), primary and secondary amines, alkoxides, and thiolates can displace the chloride to produce 4-amino-2-(pyridin-2-yl)pyrimidine derivatives with diverse 6-substituents. Reactions are typically performed in polar aprotic solvents such as DMF, DMSO, or NMP in the presence of a base (e.g., Et₃N, K₂CO₃, or DIPEA). Reaction temperatures and times should be optimized empirically.

Transition-Metal-Catalyzed Cross-Coupling: The aryl chloride can also participate in palladium-catalyzed reactions, including Suzuki–Miyaura coupling (with arylboronic acids), Buchwald–Hartwig amination, and Negishi coupling, enabling access to biaryl and N-aryl pyrimidine scaffolds relevant to drug discovery.

Functionalization of the Amino Group: The 4-amino group may be acylated with acid chlorides or anhydrides, or sulfonylated with sulfonyl chlorides, to introduce additional pharmacophoric elements. Condensation with carbonyl compounds may also be employed to prepare imine or amidine derivatives.

General Protocol Outline for SNAr:

1. Dissolve 6-Chloro-2-(pyridin-2-yl)pyrimidin-4-amine (1.0 equiv) in anhydrous DMF (0.2–0.5 M).
2. Add the nucleophile (1.1–2.0 equiv) and base (1.5–3.0 equiv).
3. Heat at 80–100 °C under inert atmosphere; monitor by TLC or LC-MS.
4. Upon completion, cool, dilute with ethyl acetate, wash with water and brine, dry over Na₂SO₄, filter, and concentrate.
5. Purify by silica gel column chromatography or recrystallization.

All conditions should be validated in the researcher's specific laboratory context. Aladdin Scientific provides this guideline for informational purposes only.

Quality, Purity, and Analytical Verification

Each lot of 6-Chloro-2-(pyridin-2-yl)pyrimidin-4-amine (C189325) supplied by Aladdin Scientific is accompanied by a Certificate of Analysis (CoA) detailing purity (typically assessed by HPLC), identity confirmation (NMR or MS), and lot-specific physical data. Researchers should download and review the CoA for each individual lot prior to use.

Recommended Analytical Checks:

• Identity: Confirm by ¹H NMR and ¹³C NMR in DMSO-d₆ or CDCl₃. Key signals include aromatic protons in the 7–9 ppm region, the pyrimidine ring proton at C-5, and the broad NH₂ signal.
• Purity: Reverse-phase HPLC (C18 column, acetonitrile/water gradient with 0.1% TFA or formic acid) is appropriate for purity assessment.
• Mass Confirmation: ESI-MS should show [M+H]⁺ consistent with M = 206.63 g/mol (exact mass to be confirmed on CoA).
• Melting Point: Measure and compare against CoA specification as a rapid identity check.

If analytical results deviate significantly from CoA specifications, contact Aladdin Scientific customer service with the lot number for technical support or replacement under the applicable returns policy.

Ordering, Packaging, and Customer Support

How to Order: 6-Chloro-2-(pyridin-2-yl)pyrimidin-4-amine is available from Aladdin Scientific under SKU C189325. Place orders through the Aladdin Scientific website, via your institutional procurement system using the SKU, or by contacting your regional Aladdin Scientific sales representative. Bulk quantities and custom pack sizes may be available on request — contact customer service for pricing and lead times.

Packaging: Standard packaging formats protect the compound from moisture and light during shipping. Confirm available pack sizes on the product page at the time of ordering, as offerings may vary by region and availability.

Shipping and Storage on Receipt: Upon receipt, inspect the package for damage and verify the lot number against your order. Transfer immediately to appropriate storage conditions as specified on the label and CoA. For international shipments, confirm compliance with import regulations for research chemicals in your jurisdiction.

Returns and Technical Support: If the product does not meet CoA specifications or arrives damaged, contact Aladdin Scientific customer service within the timeframe specified in the returns and refunds policy. Provide the order number, lot number, and a description of the issue. Technical inquiries regarding application of this compound may also be directed to the Aladdin Scientific technical support team.