5-Bromo-4-chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine FAQs
5-Bromo-4-chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine FAQs
5-Bromo-4-chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine is a halogenated bicyclic heterocyclic compound widely employed as a versatile synthetic building block in medicinal chemistry, particularly in the preparation of kinase-targeted small-molecule drug candidates.
- Product SKU
- B586870
- Chemical Name
- 5-Bromo-4-chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine
- Core Scaffold
- Pyrrolo[2,3-d]pyrimidine (7-deazapurine)
- Key Functional Groups
- C4-chloro (electrophilic substitution site), C5-bromo (cross-coupling site), N7-methyl (ring nitrogen protection)
- Primary Application
- Synthetic intermediate for kinase inhibitors and other bioactive heterocyclic compounds
- Recommended Storage
- Cool, dry, well-ventilated location away from light and moisture; refer to SDS for full guidance
Overview and Chemical Identity
5-Bromo-4-chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine (Aladdin SKU: B586870) belongs to the pyrrolo[2,3-d]pyrimidine class of bicyclic heteroaromatics, also known as 7-deazapurine scaffolds. The molecule features three strategically positioned substituents: a bromine atom at C5, a chlorine atom at C4, and a methyl group on the N7 nitrogen of the pyrrole ring.
The C4-chloro group is an activated electrophilic site amenable to nucleophilic aromatic substitution (SNAr) with amines, alcohols, and thiol nucleophiles. The C5-bromo substituent serves as an excellent handle for palladium-catalyzed cross-coupling reactions, including Suzuki–Miyaura, Negishi, and Sonogashira couplings. The N7-methyl group locks the ring nitrogen in the methylated state, preventing unwanted N-H tautomerism and modulating the electronic character of the scaffold.
Synthetic Applications in Medicinal Chemistry
The pyrrolo[2,3-d]pyrimidine scaffold is a privileged structure in drug discovery because it mimics the purine core of adenosine triphosphate (ATP) while allowing extensive chemical diversification. Compounds derived from this scaffold have been explored as inhibitors of protein kinases, including Janus kinases (JAKs), epidermal growth factor receptor (EGFR), and other therapeutically relevant enzymes.
5-Bromo-4-chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine is particularly valued because its two electrophilic/cross-coupling-reactive halogen atoms allow sequential, orthogonal functionalization. A typical synthetic strategy involves first performing SNAr at C4 to install an amino or alkoxy group, followed by a palladium-mediated coupling at C5 to append an aryl, alkenyl, or alkynyl fragment, enabling efficient access to structurally diverse analogue libraries.
Handling, Safety and Storage
As with all halogenated heterocyclic intermediates, appropriate laboratory safety precautions should be observed when handling 5-Bromo-4-chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine. Personnel should wear suitable personal protective equipment (PPE), including chemical-resistant gloves, safety glasses, and a laboratory coat. Operations that generate dust or aerosols should be performed in a well-ventilated fume hood.
The compound should be stored in a tightly sealed container in a cool, dry, and well-ventilated area, protected from light and moisture. Consult the current Safety Data Sheet (SDS) provided by Aladdin Scientific for complete hazard classification, first-aid measures, and disposal guidance before use. The SDS is available upon request and on the product page.
Quality, Purity and Specifications
Aladdin Scientific supplies 5-Bromo-4-chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine (SKU: B586870) as a research-grade reagent. Researchers requiring specific purity data, analytical certificates, or batch-specific specifications—such as HPLC purity, NMR confirmation, and melting point—should request a Certificate of Analysis (CoA) for the relevant lot number.
If your application demands a higher purity grade or custom quantity, please contact Aladdin Scientific's technical sales team to discuss available options. Procurement teams can obtain bulk pricing and lead-time information through the standard quotation process.
Ordering and Technical Support
5-Bromo-4-chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine can be ordered directly from Aladdin Scientific using SKU B586870. Orders can be placed online through the Aladdin Scientific website, via purchase order, or by contacting our customer service team.
For technical questions regarding reaction conditions, compatibility with downstream synthetic steps, or regulatory documentation, researchers are encouraged to reach out to Aladdin Scientific's technical support team. We can also assist with sourcing structurally related pyrrolopyrimidine analogues or custom synthesis inquiries.
Frequently asked questions
What is 5-Bromo-4-chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine used for in research?
This compound is primarily used as a synthetic building block in medicinal chemistry. Its halogenated pyrrolo[2,3-d]pyrimidine scaffold serves as a key intermediate for the preparation of kinase inhibitors and other biologically active heterocyclic molecules, exploiting the C4-chloro group for nucleophilic aromatic substitution and the C5-bromo group for palladium-catalyzed cross-coupling reactions.
How should the C4-chloro and C5-bromo substituents be selectively functionalized?
The two halogens exhibit orthogonal reactivity: the C4-chloro group is typically more electrophilic and undergoes nucleophilic aromatic substitution (SNAr) with nitrogen, oxygen, or sulfur nucleophiles under mild to moderate conditions. The C5-bromo group, being an aryl bromide on the electron-rich pyrrole ring, is well-suited for palladium-catalyzed cross-coupling reactions such as Suzuki–Miyaura or Sonogashira couplings. Sequential functionalization—SNAr first, then cross-coupling—is a common strategy for building diverse analogue libraries.
What are the recommended storage conditions for SKU B586870?
The compound should be stored in a tightly sealed container in a cool, dry, well-ventilated area, protected from light and moisture. For complete and authoritative storage and safety guidance, always refer to the current Safety Data Sheet (SDS) available from Aladdin Scientific for this product.
How do I obtain a Certificate of Analysis (CoA) for lot-specific purity data?
You can request a Certificate of Analysis for SKU B586870 by contacting Aladdin Scientific's customer service team and providing your lot number. The CoA typically includes HPLC purity, NMR data, and other characterization information specific to the manufactured batch.
Is this compound suitable for large-scale or GMP synthesis?
SKU B586870 is supplied as a research-grade reagent intended for laboratory research use. For large-scale, GMP, or regulatory-grade requirements, please contact Aladdin Scientific's technical sales team to discuss custom synthesis, higher-grade material supply options, and associated documentation.
References
- General reference: Pyrrolo[2,3-d]pyrimidine scaffolds in kinase inhibitor design — textbook-level knowledge; no specific citation available from source material.
- Aladdin Scientific product page for 5-Bromo-4-chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine, SKU B586870.
Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
危险品化学品经营许可证（带存储）