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Updated: May 10, 2026
05:07
Microwave-Assisted Preparation of 1-Aryl-1H-pyrazole-5-amines
Published on: June 23, 2019
7-Chloro-5-methyl-2-phenyl-pyrazolo-[1,5-a]pyrimidine
Ibtissam Bassoude1, Sabine Berteina-Raboin, El Mokhtar Essassi
1Laboratoire de Chimie Organique Hétérocyclique URAC21, Pôle de Compétences Pharmacochimie, Université Mohammed V-Agdal, Avenue Ibn Battouta, BP 1014, Rabat, Morocco ; Institut de Chimie Organique et Analytique, Université d'Orléans, UMR CNRS 6005, BP 6759, 45067 Orléans Cedex 2, France.
Summary
This study details the molecular structure of C13H10ClN3, revealing near-planar fused pyrazole and pyrimidine rings. The fused system also shows near-coplanarity with the attached phenyl ring, indicating a specific molecular conformation.
Area of Science:
- Crystallography
- Organic Chemistry
- Materials Science
Background:
- Understanding the three-dimensional structure of organic molecules is crucial for predicting their properties and reactivity.
- Fused heterocyclic compounds often exhibit unique electronic and biological activities.
- The specific compound C13H10ClN3 belongs to a class of molecules with potential applications in various fields.
Purpose of the Study:
- To elucidate the precise crystal structure and molecular geometry of the title compound, C13H10ClN3.
- To analyze the spatial arrangement and planarity of the fused pyrazole-pyrimidine ring system and its relation to the phenyl substituent.
- To provide foundational structural data for further research into the compound's properties and potential uses.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the atomic coordinates and unit cell parameters.
- Crystallographic analysis was performed to calculate bond lengths, bond angles, and dihedral angles.
- Molecular modeling and visualization tools were used to assess the planarity and relative orientation of the ring systems.
Main Results:
- The fused pyrazole and pyrimidine rings within C13H10ClN3 were found to be nearly coplanar, with a small dihedral angle of 0.8(2)° between their planes.
- The mean plane of the fused heterocyclic system exhibited near-coplanarity with the pendant phenyl ring, indicated by a dihedral angle of 9.06(7)°.
- The crystal structure confirmed the molecular formula C13H10ClN3 and provided precise interatomic distances and angles.
Conclusions:
- The title compound C13H10ClN3 possesses a largely planar fused ring system, with the phenyl group adopting a nearly coplanar orientation.
- This specific molecular conformation is critical for understanding intermolecular interactions and solid-state packing.
- The detailed structural insights pave the way for targeted synthesis and application development of related heterocyclic compounds.
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