7-Aminopyrazolo[1,5-a]pyrimidine-3,6-dicarbonitrile: Properties & Uses
7-Aminopyrazolo[1,5-a]pyrimidine-3,6-dicarbonitrile: Properties & Uses
7-Aminopyrazolo[1,5-a]pyrimidine-3,6-dicarbonitrile is a multifunctional bicyclic heterocyclic compound bearing both an amino group and two cyano substituents, making it a valuable building block for medicinal chemistry and materials science research.
- Chemical Name
- 7-Aminopyrazolo[1,5-a]pyrimidine-3,6-dicarbonitrile
- Core Scaffold
- Bicyclic pyrazolo[1,5-a]pyrimidine fused ring system
- Key Functional Groups
- Primary amino group (–NH₂) and two nitrile groups (–CN) at positions 3 and 6
- Relevance
- Versatile heterocyclic building block for drug discovery and synthetic chemistry
- Aladdin SKU
- A698824
- Compound Class
- Aminopyrazolopyrimidine dicarbonitrile
Chemical Structure and Physicochemical Overview
7-Aminopyrazolo[1,5-a]pyrimidine-3,6-dicarbonitrile belongs to the pyrazolopyrimidine family of fused bicyclic nitrogen heterocycles. The molecule consists of a pyrazole ring fused with a pyrimidine ring through a shared nitrogen atom, forming the characteristic [1,5-a] ring junction. At position 7, a primary amino group (–NH₂) is present, while nitrile groups (–CN) occupy positions 3 and 6, conferring significant electron-withdrawing character to the aromatic system.
The combination of the electron-donating amino group and two electron-withdrawing cyano groups creates a push-pull electronic configuration within the heterocyclic core. This electronic polarization influences the compound's reactivity, solubility profile, and potential for non-covalent interactions such as hydrogen bonding and π–π stacking, all of which are relevant to its use as a synthetic intermediate and research tool.
As with most pyrazolopyrimidine derivatives, this compound is expected to be a stable crystalline solid under standard laboratory conditions. Storage under cool, dry conditions away from moisture and strong oxidising agents is recommended to preserve compound integrity.
Synthesis and Role as a Building Block
Pyrazolo[1,5-a]pyrimidine scaffolds are generally accessible through cyclocondensation reactions of 3-aminopyrazole derivatives with appropriate 1,3-biselectrophilic components such as malononitrile derivatives or vinylogous equivalents. The introduction of two cyano groups at positions 3 and 6, together with the 7-amino substituent, is typically achieved in a convergent synthetic sequence that builds the bicyclic system while simultaneously installing the desired functional groups.
The two nitrile groups offer rich downstream chemistry: they can be hydrolysed to carboxylic acids or amides, reduced to amines, cyclised to form aminothiazoles or tetrazoles, or engaged in Knoevenagel-type condensations. The 7-amino group similarly provides a handle for acylation, sulfonylation, reductive amination, and condensation with carbonyl compounds, enabling rapid diversification of the heterocyclic core.
This multifunctionality positions 7-Aminopyrazolo[1,5-a]pyrimidine-3,6-dicarbonitrile as a high-value scaffold in parallel synthesis campaigns and fragment-based drug discovery programmes.
Research Applications
Pyrazolopyrimidine derivatives constitute a well-established privileged scaffold in medicinal chemistry, with documented activity across a range of biological targets including kinases, phosphodiesterases, and adenosine receptors. The dicarbonitrile motif further enhances the electrophilic character of the ring system, potentially facilitating interactions with nucleophilic residues in enzyme active sites.
7-Aminopyrazolo[1,5-a]pyrimidine-3,6-dicarbonitrile is of interest as an intermediate for the preparation of novel heterocyclic libraries targeted at kinase inhibition, anti-infective research, and other therapeutic areas where nitrogen-rich heterocycles have demonstrated biological relevance. Its electron-deficient aromatic core may also attract interest in materials science contexts, for example in the design of fluorescent probes or organic semiconductors.
Researchers in combinatorial chemistry and high-throughput screening will appreciate the compound's dual electrophilic handles, which permit rapid generation of structurally diverse analogues from a single starting material.
Handling, Storage, and Safety Considerations
As a nitrile-containing heterocyclic compound, 7-Aminopyrazolo[1,5-a]pyrimidine-3,6-dicarbonitrile should be handled with standard laboratory precautions appropriate for fine chemical research reagents. Personal protective equipment including gloves, safety glasses, and a laboratory coat should be worn at all times during handling. Operations generating dust or aerosols should be conducted in a fume hood.
The compound should be stored in a tightly sealed container under cool, dry conditions, protected from light and moisture. Incompatibility with strong acids, bases, and oxidising agents should be considered when planning storage arrangements. Specific hazard classification data, GHS pictograms, and detailed first-aid measures should be obtained from the current Safety Data Sheet (SDS) provided by Aladdin Scientific prior to use.
Disposal of waste material should comply with applicable local and national regulations governing chemical waste management.
Frequently asked questions
What is 7-Aminopyrazolo[1,5-a]pyrimidine-3,6-dicarbonitrile used for in research?
This compound serves primarily as a synthetic building block in medicinal chemistry and combinatorial chemistry. Its amino group and two cyano groups provide multiple reactive handles for derivatisation, enabling the construction of diverse heterocyclic libraries for biological screening, including programmes targeting kinases and other therapeutically relevant enzymes.
How should 7-Aminopyrazolo[1,5-a]pyrimidine-3,6-dicarbonitrile be stored?
The compound should be stored in a tightly closed container under cool, dry conditions, away from light, moisture, and incompatible materials such as strong acids, bases, and oxidising agents. Always consult the current Safety Data Sheet supplied by Aladdin Scientific for specific storage temperature recommendations and hazard information.
What downstream reactions are possible with the cyano groups of this compound?
The two nitrile groups on 7-Aminopyrazolo[1,5-a]pyrimidine-3,6-dicarbonitrile are amenable to a wide range of transformations, including hydrolysis to carboxylic acids or primary amides, reduction to primary amines, and cycloaddition or condensation reactions to form five-membered N-heterocycles such as tetrazoles and aminothiazoles. These transformations make the compound a versatile scaffold for medicinal chemistry library synthesis.
Where can I purchase 7-Aminopyrazolo[1,5-a]pyrimidine-3,6-dicarbonitrile?
7-Aminopyrazolo[1,5-a]pyrimidine-3,6-dicarbonitrile is available from Aladdin Scientific under product SKU A698824. Please visit the Aladdin Scientific website or contact your local representative for pricing, availability, and quantity options.
References
- Comprehensive textbook-level knowledge on pyrazolo[1,5-a]pyrimidine chemistry and reactivity of nitrile functional groups in heterocyclic synthesis. No specific literature citation was identified in the source material.
- Aladdin Scientific product listing for 7-Aminopyrazolo[1,5-a]pyrimidine-3,6-dicarbonitrile, SKU A698824.
Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
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