4854-10-8

Basic information

• Product Name: 2-chloro-6-(piperidin-1-yl)-5H-purine
• CAS NO: 4854-10-8
• Molecular Formula: C₁₀H₁₂ClN₅
• Molecular Weight: 237.6888
• Mol File: 4854-10-8.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 353.2°C at 760 mmHg
• Flash Point: 167.4°C
• Density: 1.61g/cm³
• Vapor Pressure: 3.65E-05mmHg at 25°C
• Refractive Index: 1.781
• CAS DataBase Reference: 2-chloro-6-(piperidin-1-yl)-5H-purine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-chloro-6-(piperidin-1-yl)-5H-purine(4854-10-8)
• EPA Substance Registry System: 2-chloro-6-(piperidin-1-yl)-5H-purine(4854-10-8)

Safety Data

• Hazardous Substances Data: 4854-10-8(Hazardous Substances Data)

Upstream product

• 5451-40-1 2,6 dichloropurine 
• 110-89-4 piperidine 
• 10310-21-1 2-Amino-6-chloropurin 
• 73-40-5 2-amino-1,9-dihydro-6H-purin-6-one 
• 149948-30-1 N-(6-chloro-9H-purin-2-yl)formamide 

Downstream Products

• 1062204-19-6 3-(6-(piperidin-1-yl)-9H-purin-2-yl)phenol 
• 1318254-93-1 2-chloro-9-phenyl-6-(piperidin-1-yl)-9H-purine 
• 7469-13-8 (6-piperidino-7(9)H-purin-2-yl)-hydrazine 
• 1928-81-0 6-(piperidin-1-yl)purine 
• 7471-83-2 furfuryl-(6-piperidino-7(9)H-purin-2-yl)-amine 

Relevant articles and documents

Room-Temperature Amination of Chloroheteroarenes in Water by a Recyclable Copper(II)-Phosphaadamantanium Sulfonate System

Buchwald-Hartwig amination of chloroheteroarenes has been a challenging synthetic process, with very few protocols promoting this important transformation at ambient temperature. The current report discusses about an efficient copper-based catalytic system (Cu/PTABS) for the amination of chloroheteroarenes at ambient temperature in water as the sole reaction solvent, a combination that is first to be reported. A wide variety of chloroheteroarenes could be coupled efficiently with primary and secondary amines as well as selected amino acid esters under mild reaction conditions. Catalytic efficiency of the developed protocol also promotes late-stage functionalization of active pharmaceutical ingredients (APIs) such as antibiotics (floxacins) and anticancer drugs. The catalytic system also performs efficiently at a very low concentration of 0.0001 mol % (TON = 980,000) and can be recycled 12 times without any appreciable loss in activity. Theoretical calculations reveal that the π-acceptor ability of the ligand PTABS is the main reason for the appreciably high reactivity of the catalytic system. Preliminary characterization of the catalytic species in the reaction was carried out using UV-VIS and ESR spectroscopy, providing evidence for the Cu(II) oxidation state.

HFIP Promoted Low-Temperature SNAr of Chloroheteroarenes Using Thiols and Amines

A highly efficient and an unprecedented hexafluoro-2-propanol, promoting low-temperature aromatic nucleophilic substitutions of chloroheteroarenes, has been performed using thiols and (secondary) amines under base-free and metal-free conditions. The developed protocol also provides excellent regio-control for the selective functionalization of dichloroheteroarenes, while the utility of the protocol was demonstrated by the modification of a commercially available drug ceritinib.

Synthesis of Chiral Cyclopropyl Carbocyclic Purine Nucleosides via Asymmetric Intramolecular Cyclopropanations Catalyzed by a Chiral Ruthenium(II) Complex

The synthesis of chiral cyclopropyl carbocyclic purine nucleoside analogues via the highly enantioselective intramolecular cyclopropanation reactions has been reported. With a chiral ruthenium(II)-phenyloxazoline complex as the catalyst, cyclopropyl carbocyclic purine nucleoside analogues containing three contiguous stereocenters were obtained with up to 99% yield and 99% ee. Furthermore, a chiral cyclopropyl carbocyclic adenosine nucleoside having anti-BLV activity could be synthesized in a concise manner using this strategy. (Figure presented.).