18202-82-9

Basic information

• Product Name: 6-chloro-N4-(1-methylethyl)pyrimidine-4,5-diamine
• Synonyms: 6-chloro-N4-(1-methylethyl)pyrimidine-4,5-diamine;6-CHLORO-N4-(1-METHYLETHYL)-4,5-PYRIMIDINEDIAMINE;AKOS A0602-0611;6-chloro-N4-isopropylpyriMidine-4,5-diaMine
• CAS NO: 18202-82-9
• Molecular Formula: C₇H₁₁ClN₄
• Molecular Weight: 186.64204
• Mol File: 18202-82-9.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 332.4°C at 760 mmHg
• Flash Point: 154.8°C
• Appearance: /
• Density: 1.305g/cm³
• Vapor Pressure: 0.000146mmHg at 25°C
• Refractive Index: 1.622
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 6-chloro-N4-(1-methylethyl)pyrimidine-4,5-diamine(CAS DataBase Reference)
• NIST Chemistry Reference: 6-chloro-N4-(1-methylethyl)pyrimidine-4,5-diamine(18202-82-9)
• EPA Substance Registry System: 6-chloro-N4-(1-methylethyl)pyrimidine-4,5-diamine(18202-82-9)

Safety Data

• Hazardous Substances Data: 18202-82-9(Hazardous Substances Data)

Usage

Chemical Structure

Pyrimidine derivative

Potential Applications

Pharmaceutical applications

Anticancer Activity

Studied as an antiproliferative agent against cancer cells

Mechanism of Action

Acts as a kinase inhibitor

Target Enzyme

Protein kinase B (Akt)

Activity

Inhibits Akt enzyme activity

Disease Targets

Investigated for treating cancer and neurodegenerative disorders

Promising Candidate

Due to its chemical structure and activity, it shows promise for further research and potential drug development.

InChI:InChI=1/C7H11ClN4/c1-4(2)12-7-5(9)6(8)10-3-11-7/h3-4H,9H2,1-2H3,(H,10,11,12)

Upstream product

• 25710-25-2 6-chloro-N-isopropyl-5-nitropyrimidin-4-amine 
• 5413-85-4 5-amino-4,6-dichloropyridimine 
• 75-31-0 isopropylamine 

Downstream Products

• 6627-31-2 6-chloro-9-pentylpurine 

Relevant articles and documents

3,4-dichloroisothiazole heterocyclic purine derivatives as well as preparation method and application thereof

The invention provides a 3,4-dichloroisothiazole bipurine derivative as well as a preparation method and application thereof, and particularly relates to the 3,4-dichloroisothiazole bipurine derivative of which the chemical structural general formula is s

Synthesis of 6,8,9 poly-substituted purine analogue libraries as pro-apoptotic inducers of human leukemic lymphocytes and DAPK-1 inhibitors

A 18-member library of 6,8,9-poly-substituted purines was prepared from pyrimidines, primary alcohols, and N,N-dimethylamides under basic conditions via a novel one-pot synthetic pathway controlled by amide sizes and the novel analogues were tested against two leukemia cell lines: Jurkat (acute T cell leukemia) and K562 (chronic erythroleukemia) cells. Compounds having a benzoxy group at C6 position of the aromatic ring exhibited antiproliferative activity in Jurkat cells whereas all compounds induced a lower effect on K562 cells. Analysis of cell cycle, Annexin-V staining, and cleavage of initiator caspases assays showed that the active purine analogues induce cell death by apoptosis. Based on these results, a new purine derivative was synthesized, 6-benzyloxy-9-tert-butyl-8-phenyl-9H-purine (6d), which displayed the highest activity of the series against Jurkat cell lines. Finally, 33P-radiolabeled kinase assays using 96 recombinant human kinases known to be involved in apoptotic events were performed. Just one of the kinases tested, DAPK-1, was inhibited 50% or more by the phenotypic hits at 10 μM, suggesting that the inhibition of this target could be responsible for the induction of cell death by apoptosis. In agreement with the phenotypic results, the most active antiproliferative agent, 6d, displayed also the lowest IC50 value against recombinant DAPK1 (2.5 μM), further supporting the potential role of this protein on the observed functional response. DAPK-1 inhibition led by 6d together with its pro-apoptotic properties against the Jurkat line makes it an interesting candidate to further investigate the role of DAPK1 kinase in triggering apoptosis in cancer cells, a role which is attracting recent interest.

An efficient one-pot synthesis of 6-alkoxy-8,9-dialkylpurines via reaction of 5-amino-4-chloro-6-alkylaminopyrimidines with N,N-dimethylalkaneamides and alkoxide ions

The synthesis of a number of new 6-alkoxy-8,9-(disubstituted)purines has been accomplished by the cyclization of the corresponding intermediate 5-amino-4-chloro-6-(alkylamino)pyrimidines promoted by alkoxides and various N,N-dimethyl amides, where the latter act as solvent-reagents. By this three-component condensation reaction we are able to introduce an alkyl group in the 8 position of the purine ring with the concomitant nucleophilic replacement of the 6-chloro group with an alkoxy moiety.