5449-10-5

Basic information

• Product Name: 6-chloro-N~4~-cyclohexylpyrimidine-4,5-diamine
• Synonyms: 4,5-pyrimidinediamine, 6-chloro-N~4~-cyclohexyl-; 6-Chloro-N~4~-cyclohexylpyrimidine-4,5-diamine
• CAS NO: 5449-10-5
• Molecular Formula: C₁₀H₁₅ClN₄
• Molecular Weight: 226.7059
• Mol File: 5449-10-5.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 400.7°C at 760 mmHg
• Flash Point: 196.1°C
• Density: 1.317g/cm³
• Vapor Pressure: 1.25E-06mmHg at 25°C
• Refractive Index: 1.642
• CAS DataBase Reference: 6-chloro-N~4~-cyclohexylpyrimidine-4,5-diamine(CAS DataBase Reference)
• NIST Chemistry Reference: 6-chloro-N~4~-cyclohexylpyrimidine-4,5-diamine(5449-10-5)
• EPA Substance Registry System: 6-chloro-N~4~-cyclohexylpyrimidine-4,5-diamine(5449-10-5)

Safety Data

• Hazardous Substances Data: 5449-10-5(Hazardous Substances Data)

Usage

Substituent

Chlorine (Cl) at the 6 position

Derivative

Derived from cyclohexylpyrimidine-4,5-diamine

Potential Applications

Pharmaceuticals
Agrochemicals

Uses

Building block in synthesis of biologically active compounds
Precursor for drug or pesticide development
Intended application
Chemical reactions undergone

Upstream product

• 5413-85-4 5-amino-4,6-dichloropyridimine 
• 108-91-8 cyclohexylamine 

Downstream Products

• 5452-41-5 6-chloro-9-cyclohexyl-9H-purine 

Relevant articles and documents

A One-Pot Synthesis of Highly Functionalized Purines

Highly substituted purines were synthesized in good to high yields through a one-pot straightforward metal-free scalable method, using the Traube synthesis adapted to Vilsmeier-type reagents. From 5-amino-4-chloropyrimidines, new 9-aryl-substituted chloropurines and intermediates for peptide nucleic acid synthesis were prepared. Variant procedures allowing a rapid synthesis of ribonucleosides and 7-benzylpurine from 5-amidino-6-aminopyrimidines are also reported to illustrate the high potential of this versatile toolbox. This route appears to be particularly interesting in the field of nucleic acids for a direct and rapid access to various new 8-alkylpurine nucleosides.

Enhanced selectivity for inhibition of analog-sensitive protein kinases through scaffold optimization

The ability to inhibit any protein kinase of interest with a small molecule is enabled by a combination of genetics and chemistry. Genetics is used to modify the active site of a single kinase to render it distinct from all naturally occurring kinases. Next, organic synthesis is used to develop a small molecule, which does not bind to wild-type kinases but is a potent inhibitor of the engineered kinase. This approach, termed chemical genetics, has been used to generate highly potent mutant kinase-specific inhibitors based on a pyrazolopyrimidine scaffold. Here, we asked if the selectivity of the resulting pyrazolopyrimidines could be improved, as they inhibit several wild-type kinases with low-micromolar IC50 values. Our approach to improve the selectivity of allele-specific inhibitors was to explore a second kinase inhibitor scaffold. A series of 6,9-disubstituted purines was designed, synthesized, and evaluated for inhibitory activity against several kinases in vitro and in vivo. Several purines proved to be potent inhibitors against the analog-sensitive kinases and exhibited greater selectivity than the existing pyrazolopyrimidines.

Triazolo [4,5-d]-pyrimidines

This disclosure relates to the method for the treatment of psoriasis which comprises the topical administration to a mammal suffering from psoriasis of an effective dose for treating psoriasis of a 7X-5Q-3Y-3H-γ-triazolo[4,5-d]-pyrimidine wherein X is hal