(4,5,6,7-Tetrahydropyrazolo[1,5-a]pyrazin-2-yl)methanol: Lab Protocol Guide

(4,5,6,7-Tetrahydropyrazolo[1,5-a]pyrazin-2-yl)methanol is a bicyclic heterocyclic compound featuring a partially saturated pyrazolopyrazine core bearing a primary hydroxymethyl group, making it a versatile scaffold and intermediate in medicinal chemistry and drug discovery research.

Product Name

(4,5,6,7-Tetrahydropyrazolo[1,5-a]pyrazin-2-yl)methanol

SKU

M730314

Core Structure

Bicyclic pyrazolo[1,5-a]pyrazine with tetrahydro saturation at positions 4,5,6,7

Functional Group

Primary hydroxymethyl (-CH2OH) at position 2 of the pyrazole ring

Primary Application

Medicinal chemistry scaffold, synthetic building block for drug discovery

Supplier

Aladdin Scientific

Compound Overview and Structural Features

(4,5,6,7-Tetrahydropyrazolo[1,5-a]pyrazin-2-yl)methanol (Aladdin SKU: M730314) is a bicyclic nitrogen-containing heterocycle composed of a pyrazole ring fused to a piperazine-like ring system, with partial saturation at the 4,5,6,7-positions. The compound carries a primary hydroxymethyl group at the 2-position of the pyrazole moiety.

The combination of two basic nitrogen atoms within the bicyclic framework and the freely reactive hydroxymethyl handle makes this compound highly attractive as a synthetic intermediate. The hydroxymethyl group can be further elaborated via oxidation to an aldehyde or carboxylic acid, esterification, or conversion to activated leaving groups for nucleophilic substitution reactions.

The partial saturation of the ring system confers three-dimensional character compared to fully aromatic analogues, a property increasingly valued in modern drug discovery to improve selectivity and physicochemical properties of candidate molecules.

Safety, Handling, and Storage

Personal Protective Equipment (PPE): When handling (4,5,6,7-Tetrahydropyrazolo[1,5-a]pyrazin-2-yl)methanol, wear appropriate laboratory PPE including nitrile gloves, safety goggles, and a lab coat. Work in a well-ventilated area or fume hood where possible.

Storage: Store the compound in a tightly sealed container in a cool, dry location away from direct light and incompatible materials such as strong oxidizers. Specific storage temperature recommendations should be confirmed on the product Certificate of Analysis (CoA) supplied with SKU M730314.

Disposal: Dispose of waste material in accordance with local institutional and governmental regulations for nitrogen-containing heterocyclic compounds. Do not pour down the drain without verification of local disposal guidelines.

First Aid: In case of skin or eye contact, rinse immediately with copious water for at least 15 minutes and seek medical attention. If ingested or inhaled, remove the affected individual to fresh air and consult a physician or poison control center promptly.

Solution Preparation Protocol

The following protocol describes recommended practices for dissolving and preparing working solutions of (4,5,6,7-Tetrahydropyrazolo[1,5-a]pyrazin-2-yl)methanol (M730314).

1. Solvent Selection: Due to the presence of the hydroxymethyl group and the basic nitrogen atoms, this compound is expected to show good solubility in polar protic solvents such as water and methanol, and polar aprotic solvents such as DMSO and DMF. Solubility should be empirically verified for each new lot.
2. Stock Solution Preparation: Weigh the required amount of compound using a calibrated analytical balance. Transfer to an appropriate glass vial. Add solvent gradually with vortex mixing or brief sonication until fully dissolved. Prepare stock solutions at concentrations appropriate for the intended downstream application.
3. Filtration: If particulates are observed, filter the solution through a 0.22 µm PTFE or nylon syringe filter prior to use.
4. Storage of Solutions: Store prepared solutions in tightly capped vials, protected from light. For long-term storage, aliquot to minimize freeze-thaw cycles. Confirm stability under specific storage conditions on the CoA before extended storage.
5. Concentration Verification: Where accuracy is critical, verify solution concentration by UV-Vis absorbance or other appropriate analytical method.

Note: Specific solubility data and recommended concentrations are not provided in the current source material. Verify empirically and consult the product CoA for lot-specific data.

Research Applications

(4,5,6,7-Tetrahydropyrazolo[1,5-a]pyrazin-2-yl)methanol is primarily valued in synthetic and medicinal chemistry as a versatile building block. The following applications represent common uses of such bicyclic hydroxymethyl-bearing heterocycles:

• Drug Discovery Scaffolds: The tetrahydropyrazolopyrazine core provides a sp3-enriched, three-dimensional scaffold useful for constructing kinase inhibitors, GPCR ligands, and other pharmacological agents where ring saturation improves selectivity and metabolic stability.
• Synthetic Intermediate: The primary alcohol at position 2 serves as a handle for further chemical elaboration, including oxidation to aldehyde/acid, Mitsunobu reactions, mesylation or tosylation for displacement reactions, and coupling to other fragments.
• Fragment-Based Drug Discovery (FBDD): Low-molecular-weight bicyclic fragments bearing polar functional groups are frequently employed in FBDD campaigns to identify novel binding interactions with target proteins.
• Combinatorial Chemistry: As a building block in parallel synthesis or combinatorial library generation, the compound enables the rapid production of structurally diverse analogues for SAR studies.

Note: Specific published applications of M730314 in peer-reviewed literature were not identified in the source material. The above applications are based on the compound class. Researchers should conduct a primary literature search to identify the most relevant use cases.

Quality, Purity, and Ordering Information

Aladdin Scientific supplies (4,5,6,7-Tetrahydropyrazolo[1,5-a]pyrazin-2-yl)methanol under SKU M730314. Each lot is accompanied by a Certificate of Analysis (CoA) documenting identity, purity, and appearance specifications determined by standard analytical techniques including NMR, HPLC, and/or mass spectrometry.

Ordering: M730314 can be ordered directly through the Aladdin Scientific website or by contacting your regional Aladdin sales representative. Bulk quantities and custom packaging may be available upon request.

Purity Verification: Researchers are advised to review the CoA for the specific lot received and, where critical, to perform independent purity verification by HPLC or NMR prior to use in quantitative assays.

Returns and Quality Concerns: If the product does not meet stated specifications, contact Aladdin Scientific customer service with the lot number and CoA details to initiate a return or replacement request in accordance with Aladdin's returns and refund policy.

Frequently asked questions

What solvents are recommended for dissolving (4,5,6,7-Tetrahydropyrazolo[1,5-a]pyrazin-2-yl)methanol?

Based on the compound's structural features — including the hydroxymethyl group and basic nitrogen atoms — good solubility is expected in polar protic solvents such as water and methanol, and polar aprotic solvents such as DMSO and DMF. However, empirical solubility testing is recommended for each lot, and researchers should consult the product CoA for lot-specific guidance.

What is the primary use of (4,5,6,7-Tetrahydropyrazolo[1,5-a]pyrazin-2-yl)methanol in research?

This compound is primarily used as a synthetic building block and scaffold in medicinal chemistry and drug discovery. Its bicyclic, sp3-enriched framework and reactive hydroxymethyl group make it suitable for constructing structurally diverse compound libraries for SAR studies, as well as serving as an intermediate in multi-step syntheses targeting pharmacologically active molecules.

How should (4,5,6,7-Tetrahydropyrazolo[1,5-a]pyrazin-2-yl)methanol be stored to maintain stability?

The compound should be stored in a tightly sealed container in a cool, dry place, away from light and incompatible materials such as strong oxidizing agents. For long-term storage of prepared solutions, aliquoting to avoid repeated freeze-thaw cycles is advised. Consult the Certificate of Analysis provided with SKU M730314 for lot-specific storage temperature recommendations.

What analytical methods are used to confirm the identity and purity of M730314?

Aladdin Scientific employs standard analytical techniques including nuclear magnetic resonance spectroscopy (NMR), high-performance liquid chromatography (HPLC), and mass spectrometry to characterize and confirm the identity and purity of each lot of M730314. Detailed results are reported in the lot-specific Certificate of Analysis.

References

1. Aladdin Scientific. Product Information: (4,5,6,7-Tetrahydropyrazolo[1,5-a]pyrazin-2-yl)methanol, SKU M730314. Aladdin Scientific catalog.
2. Lovering, F.; Bikker, J.; Humblet, C. Escape from Flatland: Increasing Saturation as an Approach to Improving Clinical Success. J. Med. Chem. 2009, 52, 6752–6756. doi:10.1021/jm901241e
3. Erlanson, D. A.; Fesik, S. W.; Hubbard, R. E.; Jahnke, W.; Jhoti, H. Twenty years on: the impact of fragments on drug discovery. Nat. Rev. Drug Discov. 2016, 15, 605–619. doi:10.1038/nrd.2016.109

Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.