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

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.

8-Bromo-9-alkyl adenine derivatives as tools for developing new adenosine A2A and A2B receptors ligands

Importance of making available selective adenosine receptor antagonists is boosted by recent findings of adenosine involvement in many CNS dysfunctions. In the present work a series of 8-bromo-9-alkyl adenines are prepared and fully characterized in radio

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.

6-(alkylamino)-9-alkylpurines. A new class of potential antipsychotic agents

A series of 6-(alkylamino)-9-alkylpurines was synthesized and evaluated for the property of antagonizing the behavioral effects in animals of the dopamine agonist apomorphine. This model for identifying potential antipsychotic agents is based on the hypothesis that agents that antagonize apomorphine-induced aggressive behavior in rats and apomorphine-induced climbing in mice, but that do not block stereotyped behavior, could have an antipsychotic effect in humans without producing extrapyramidal side effects. The antiaggressive-behavior activity of lead compound 1 (6-(dimethylamino)- 9-(3-phenylalaninamidobenzyl)-9H-purine) was improved 48-fold with 6- (cyclopropylamino)-9-(cyclopropylmethyl)-2-(trifluoromethyl)-9H-purine (80) (po ED50 of 2 mg/kg), which was obtained through an iterative sequence of structure-activity relationship studies that encompassed evaluation of the effects of structure variations at the purine 9-, 6-, and 2-positions. Potency was enhanced with a 9-cyclopropyl group, the duration of action was improved with the 6-(cyclopropylamino) substituent, potency was further enhanced with an N-formyl prodrug, and an agent with reduced cardiovascular effect emerged with the 2-trifluoromethyl purine 80. This potential antipsychotic agent was not developed further due to undesirable effects on the stomach.

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