2-Allyl-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one
[CAS# 955368-90-8]

Identification

• Classification: Organic raw materials >> Ketone compound
• Name: 2-Allyl-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one
• Synonyms: 6-methylsulfanyl-2-prop-2-enyl-1H-pyrazolo[3,4-d]pyrimidin-3-one
• Molecular Formula: C₉H₁₀N₄OS
• Molecular Weight: 222.27
• CAS Registry Number: 955368-90-8
• SMILES: CSC1=NC=C2C(=N1)NN(C2=O)CC=C

Properties

• Density: 1.4±0.1 g/cm³ Calc.^*
• Boiling point: 397.9±44.0 °C 760 mmHg (Calc.)^*
• Flash point: 194.4±28.4 °C (Calc.)^*
• Index of refraction: 1.662 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H320-H335
• Safety Statements: P261-P280-P301+P312-P302+P352-P305+P351+P338

Discovery and Applications

2-Allyl-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one is a fused heterocyclic compound consisting of a pyrazolo[3,4-d]pyrimidine core substituted with an allyl group at the 2-position and a methylthio group at the 6-position. The bicyclic framework combines the electronic properties of pyrazole and pyrimidine, providing a planar aromatic system capable of hydrogen bonding, π–π stacking, and coordination with metal centers. The allyl substituent introduces a reactive site for further functionalization, while the methylthio group modulates electronic density and lipophilicity, enhancing chemical versatility.

The synthesis of 2-allyl-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one generally involves cyclization of suitably substituted hydrazine and β-ketoamide precursors to form the pyrazolo[3,4-d]pyrimidine ring, followed by selective alkylation at the 2-position and methylthiolation at the 6-position. Reaction conditions are optimized to maintain regioselectivity and prevent overreaction at the heterocyclic nitrogen atoms. The final product is typically purified by recrystallization or chromatographic separation to obtain a solid suitable for further chemical or biological applications.

In organic synthesis, this compound serves as a versatile intermediate for the preparation of substituted pyrazolo[3,4-d]pyrimidines and more complex heterocycles. The allyl group can undergo palladium-catalyzed cross-coupling, epoxidation, or radical reactions, allowing introduction of diverse substituents. The methylthio group provides a handle for oxidation to sulfoxides or sulfones, enabling modulation of polarity and reactivity in downstream derivatives.

In medicinal chemistry, derivatives of 2-allyl-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one are investigated for their potential as enzyme inhibitors, receptor ligands, or kinase modulators. The pyrazolo[3,4-d]pyrimidine scaffold is known for its bioactivity, and the substituents can be tailored to influence binding affinity, solubility, and metabolic stability. The methylthio group, in particular, can participate in hydrophobic interactions within enzyme active sites, while the allyl group allows derivatization for structure–activity relationship studies.

The compound is also relevant in methodology research. Its multifunctional nature allows chemists to study selective C–C and C–S bond formation, heterocyclic functionalization, and protective group strategies. It serves as a model substrate for developing new synthetic routes to nitrogen-rich heterocycles with potential applications in medicinal and materials chemistry.

Physically, 2-allyl-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one is typically obtained as a solid with moderate solubility in polar organic solvents such as dimethylformamide, ethanol, and dichloromethane. It is stable under standard laboratory conditions but should be protected from strong acids, strong bases, and oxidizing agents that could modify the methylthio or heterocyclic functionalities. Proper storage ensures chemical integrity for synthetic and biological applications.

Overall, 2-allyl-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one is a multifunctional heterocyclic compound featuring a pyrazolo[3,4-d]pyrimidine core with reactive allyl and methylthio substituents. Its structural features enable selective chemical transformations and derivatization, making it a valuable intermediate for the synthesis of bioactive molecules, functional heterocycles, and complex organic targets in medicinal and synthetic chemistry.

References

2024. Novel pyrimido-heterocyclic novel compound serving as wee1 inhibitor and application thereof. World Intellectual Property Organization.
URL: WO-2024146502-A1

2023. Pyrimido macroheterocyclic compound as wee1-yes dual-target inhibitor and use thereof. World Intellectual Property Organization.
URL: WO-2023217201-A2

2024. A tricyclic compound of WEE1 inhibitor and its preparation method and use. World Intellectual Property Organization.
URL: WO-2024230807-A1