73840-54-7

Basic information

• Product Name: N-Phenethyl-6-chloropyrimidine-4,5-diamine
• Synonyms: 4-(Phenethylamino)-6-chloro-5-pyrimidinamine;6-Chloro-4-phenethylaminopyrimidin-5-amine;N-Phenethyl-6-chloropyrimidine-4,5-diamine;6-Chloro-N4-phenethyl-pyriMidine-4,5-diaMine
• CAS NO: 73840-54-7
• Molecular Formula: C₁₂H₁₃ClN₄
• Molecular Weight: 248.7114
• Mol File: 73840-54-7.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 459.5°Cat760mmHg
• Flash Point: 231.7°C
• Appearance: /
• Density: 1.331g/cm³
• Vapor Pressure: 1.26E-08mmHg at 25°C
• Refractive Index: 1.676
• PKA: 2.63±0.10(Predicted)
• CAS DataBase Reference: N-Phenethyl-6-chloropyrimidine-4,5-diamine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Phenethyl-6-chloropyrimidine-4,5-diamine(73840-54-7)
• EPA Substance Registry System: N-Phenethyl-6-chloropyrimidine-4,5-diamine(73840-54-7)

Safety Data

• Hazardous Substances Data: 73840-54-7(Hazardous Substances Data)

Usage

InChI:InChI=1/C12H13ClN4/c13-11-10(14)12(17-8-16-11)15-7-6-9-4-2-1-3-5-9/h1-5,8H,6-7,14H2,(H,15,16,17)

Upstream product

• 5413-85-4 5-amino-4,6-dichloropyridimine 
• 64-04-0 phenethylamine 

Downstream Products

• 201541-68-6 7-chloro-3-phenethyl-3H-[1,2,3]triazolo[4,5-d]pyrimidine 
• 1151917-25-7 5-(6-chloro-9-phenethyl-9H-purin-8-yl)-furan-2-sulfonic acid 
• 213248-11-4 diethyl [5-(6-chloro-9-phenethyl-9H-purin-8-yl)-furan-2-yl]-phosphonate 
• 1020112-31-5 4-chloro-5-(N-4-bromobutanoyl)amino-6-phenetylaminopyrimidine 
• 34396-75-3 9-phenethyl-1,9-dihydro-purin-6-one 

Relevant articles and documents

Synthesis and screening of 6-alkoxy purine analogs as cell type-selective apoptotic inducers in Jurkat cells

Purines are ubiquitous structures in cell biology involved in a multitude of cellular processes, because of which substituted purines and analogs are considered excellent scaffolds in drug design. In this study, we explored the key structural features of a purine-based proapoptotic hit, 8-tert-butyl-9-phenyl-6-benzyloxy-9H-purine (1), by setting up a library of 6-alkoxy purines with the aim of elucidating the structural requirements that govern its biological activity and to study the cell selectivity of this chemotype. This was done by a phenotypic screening approach based on cell cycle analysis of a panel of six human cancer cell lines, including T cell leukemia Jurkat cells. From this study, two derivatives (12 and 13) were identified as Jurkat-selective proapoptotic compounds, displaying superior potency and cell selectivity than hit 1.

COMPOUNDS FOR TREATING CYSTIC FIBROSIS

The present invention relates to compounds of Formula (I) or pharmaceutically acceptable enantiomers, salts, solvates or prodrugs thereof. The invention further relates to the use of the compounds of Formula (I) for the treatment of cystic fibrosis. The invention also relates to a process for manufacturing compounds of Formula (I).

An unexpected cyclization discovered during the synthesis of 8-substituted purines from a 4,5-diaminopyrimidine

Attempted conversion of 4-chloro-5-(N-4-bromobutanoyl)amino-6-phenethylaminopyrimidine (2) to 6-chloro-8-[1-(3-bromo)propyl]-9-phenethylpurine (1) under standard cyclization conditions did not give the targeted product. Instead, an unexpected cyclization