7013-21-0

Basic information

• Product Name: 2-Chloro-9-methyl-9H-purin-6-amine
• Synonyms: 2-Chloro-9-methyl-9H-purin-6-amine;6-Amino-2-chloro-9-methylpurine;2-Chloro-6-amino-9-methylpurine;2-Chloro-9-methyladenine
• CAS NO: 7013-21-0
• Molecular Formula: C₆H₆ClN₅
• Molecular Weight: 183.5983
• Mol File: 7013-21-0.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 315.6°Cat760mmHg
• Flash Point: 144.6°C
• Appearance: /
• Density: 1.79g/cm³
• Vapor Pressure: 0.000434mmHg at 25°C
• Refractive Index: 1.821
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 1.98±0.10(Predicted)
• CAS DataBase Reference: 2-Chloro-9-methyl-9H-purin-6-amine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloro-9-methyl-9H-purin-6-amine(7013-21-0)
• EPA Substance Registry System: 2-Chloro-9-methyl-9H-purin-6-amine(7013-21-0)

Safety Data

• Hazardous Substances Data: 7013-21-0(Hazardous Substances Data)

Usage

General Description

2-Chloro-9-methyl-9H-purin-6-amine, also known as 2-chloro-6-methyl-9H-purin-9-amine, is a chemical compound with the molecular formula C6H6ClN5. It is a purine derivative and has a chlorine atom and a methyl group attached to the purine ring structure. 2-Chloro-9-methyl-9H-purin-6-amine has potential applications in the field of pharmaceuticals and drug development, as it may exhibit biological activities and could be studied for its potential medicinal properties. Additionally, it may also have uses in research and analytical chemistry, serving as a reference compound or standard for various analytical techniques or methods.

InChI:InChI=1/C6H6ClN5/c1-12-2-9-3-4(8)10-6(7)11-5(3)12/h2H,1H3,(H2,8,10,11)

Synthetic route

2,6-dichloro-9-methyl-9H-purine (2382-10-7) → 2-Chloro-9-methyladenine (7013-21-0)

Conditions	Yield
With ammonium hydroxide In acetonitrile at 55℃; for 5.5h;	82%

2-chloroadenine (1839-18-5) + methyl iodide (74-88-4) → 2-Chloro-9-methyladenine (7013-21-0)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide
With tetra(n-butyl)ammonium hydroxide In dichloromethane for 1h;

2,6-dichloro-9-methyl-7(9)H-purine → 2-Chloro-9-methyladenine (7013-21-0)

Conditions	Yield
With ethanol; ammonia

2,6 dichloropurine (5451-40-1) → 2-Chloro-9-methyladenine (7013-21-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: N,N-diisopropylethylamine, NH3 / propan-1-ol / 20 h / Heating 2: K2CO3 / dimethylformamide View Scheme

2,6-dichloro-7H-purine (5451-40-1) → 2-Chloro-9-methyladenine (7013-21-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate / acetonitrile / 24 h / 20 °C 2: ammonium hydroxide / acetonitrile / 5.5 h / 55 °C View Scheme

2-Chloro-9-methyladenine (7013-21-0) + ethanolamine (141-43-5) → 2-(6-Amino-9-methyl-9H-purin-2-ylamino)-ethanol

Conditions	Yield
at 155 - 160℃; for 3h;	87%

2-Chloro-9-methyladenine (7013-21-0) → 8-bromo-2-chloro-9-methyl-9H-purin-6-amine (1436428-39-5)

Conditions	Yield
With bromine; sodium acetate trihydrate In tetrahydrofuran; methanol; water at -10 - 20℃; for 0.5h;	60%

tyrosamine (51-67-2) + 2-Chloro-9-methyladenine (7013-21-0) → 4-(2-((6-amino-9-methyl-9H-purin-2-yl)amino)ethyl)phenol (1436428-36-2)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 145℃; for 42h;	32%

2-Chloro-9-methyladenine (7013-21-0) + sodium ethanolate (141-52-6) → 2-ethoxy-9-methyl-9H-purin-6-ylamine (857400-62-5)

Conditions	Yield
With ethanol at 130℃;

2-Chloro-9-methyladenine (7013-21-0) → 3-methyladenine (700-00-5) + 9-methylpurine (20427-22-9)

Conditions	Yield
With ammonia; sodium In diethyl ether for 0.5h;	A 47 % Spectr. B n/a

2-Chloro-9-methyladenine (7013-21-0) → 8-deuterio-9-methyl-9H-purin-6-ylamine (110501-32-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 47 percent Spectr. / Na, liq. NH3 / diethyl ether / 0.5 h 2: D2O / Heating View Scheme

2-Chloro-9-methyladenine (7013-21-0) → 9-methylpurine (20427-22-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 47 percent Spectr. / Na, liq. NH3 / diethyl ether / 0.5 h 2: 46 percent Spectr. / Na, liq. NH3 / 1 h / variation of reaction time; other 6-amino- and 6-alkylamino-9-alkylpurines View Scheme

2-Chloro-9-methyladenine (7013-21-0) → 6-amino-9-methyl-3,9-dihydro-purin-2-one (54746-36-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: ethanol / 130 °C 2: PH4I; aqueous HI View Scheme

2-Chloro-9-methyladenine (7013-21-0) → 4-(2-((6-amino-8-(furan-2-yl)-9-methyl-9H-purin-2-yl)amino)ethyl)phenol (1436428-49-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: bromine; sodium acetate trihydrate / tetrahydrofuran; water; methanol / 0.5 h / -10 - 20 °C 2: caesium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,2-dimethoxyethane; water / 20.5 h / 85 °C / Inert atmosphere 3: N-ethyl-N,N-diisopropylamine / dimethyl sulfoxide / 14 h / 145 °C View Scheme

2-Chloro-9-methyladenine (7013-21-0) → 4-(2-((6-amino-9-methyl-8-(2H-1,2,3-triazol-2-yl)-9H-purin-2-yl)amino)ethyl)phenol (1436428-51-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: bromine; sodium acetate trihydrate / tetrahydrofuran; water; methanol / 0.5 h / -10 - 20 °C 2: caesium carbonate / N,N-dimethyl-formamide / 20 h / 80 °C 3: N-ethyl-N,N-diisopropylamine / dimethyl sulfoxide / 23 h / 145 °C View Scheme

2-Chloro-9-methyladenine (7013-21-0) → 2-chloro-8-(furan-2-yl)-9-methyl-9H-purin-6-amine (1436428-42-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: bromine; sodium acetate trihydrate / tetrahydrofuran; water; methanol / 0.5 h / -10 - 20 °C 2: caesium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,2-dimethoxyethane; water / 20.5 h / 85 °C / Inert atmosphere View Scheme

2-Chloro-9-methyladenine (7013-21-0) → 2-chloro-9-methyl-8-(2H-1,2,3-triazol-2-yl)-9H-purin-6-amine (1436428-45-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: bromine; sodium acetate trihydrate / tetrahydrofuran; water; methanol / 0.5 h / -10 - 20 °C 2: caesium carbonate / N,N-dimethyl-formamide / 20 h / 80 °C View Scheme

2-Chloro-9-methyladenine (7013-21-0) → ethyl 4-(4-(2-((6-amino-9-methyl-8-(2H-1,2,3-triazol-2-yl)-9H-purin-2-yl)amino)ethyl)phenoxy)butanoate (1436428-67-9)

Conditions	Yield
Multi-step reaction with 4 steps 1: bromine; sodium acetate trihydrate / tetrahydrofuran; water; methanol / 0.5 h / -10 - 20 °C 2: caesium carbonate / N,N-dimethyl-formamide / 20 h / 80 °C 3: N-ethyl-N,N-diisopropylamine / dimethyl sulfoxide / 23 h / 145 °C 4: potassium carbonate / acetone / 25 h / 20 °C / Inert atmosphere; Reflux View Scheme

2-Chloro-9-methyladenine (7013-21-0) → 4-(2-((7-amino-2-(furan-2-yl)-[1,2,4]triazolo[1,5-a][1,3,5]triazin-5-yl)amino)ethyl)phenyl butyrate (1436428-68-0)

Conditions	Yield
Multi-step reaction with 4 steps 1: bromine; sodium acetate trihydrate / tetrahydrofuran; water; methanol / 0.5 h / -10 - 20 °C 2: caesium carbonate / N,N-dimethyl-formamide / 20 h / 80 °C 3: N-ethyl-N,N-diisopropylamine / dimethyl sulfoxide / 23 h / 145 °C 4: trifluoroacetic acid / dichloromethane / 5.5 h / 20 °C View Scheme

Upstream product

• 1839-18-5 2-chloroadenine 
• 74-88-4 methyl iodide 
• 2382-10-7 2,6-dichloro-9-methyl-9H-purine 
• 5451-40-1 2,6-dichloro-7H-purine 
• 5451-40-1 2,6 dichloropurine 

Downstream Products

• 857400-62-5 2-ethoxy-9-methyl-9H-purin-6-ylamine 
• 700-00-5 3-methyladenine 
• 20427-22-9 9-methylpurine 
• 1436428-49-7 4-(2-((6-amino-8-(furan-2-yl)-9-methyl-9H-purin-2-yl)amino)ethyl)phenol 
• 1436428-51-1 4-(2-((6-amino-9-methyl-8-(2H-1,2,3-triazol-2-yl)-9H-purin-2-yl)amino)ethyl)phenol? 
• 1436428-67-9 ethyl 4-(4-(2-((6-amino-9-methyl-8-(2H-1,2,3-triazol-2-yl)-9H-purin-2-yl)amino)ethyl)phenoxy)butanoate 
• 1436428-68-0 4-(2-((7-amino-2-(furan-2-yl)-[1,2,4]triazolo[1,5-a][1,3,5]triazin-5-yl)amino)ethyl)phenyl butyrate 
• 1436428-36-2 4-(2-((6-amino-9-methyl-9H-purin-2-yl)amino)ethyl)phenol 

Relevant articles and documents

Novel adenosine A2A receptor ligands: A synthetic, functional and computational investigation of selected literature adenosine A2A receptor antagonists for extending into extracellular space

Growing evidence has suggested a role in targeting the adenosine A 2A receptor for the treatment of Parkinson's disease. The literature compounds KW 6002 (2) and ZM 241385 (5) were used as a starting point from which a series of novel ligands targeting the adenosine A2A receptor were synthesized and tested in a recombinant human adenosine A2A receptor functional assay. In order to further explore these molecules, we investigated the biological effects of assorted linkers attached to different positions on selected adenosine A2A receptor antagonists, and assessed their potential binding modes using molecular docking studies. The results suggest that linking from the phenolic oxygen of selected adenosine A2A receptor antagonists is relatively well tolerated due to the extension towards extracellular space, and leads to the potential of attaching further functionality from this position.

N6,9-Disubstituted Adenines: Potent, Selective Antagonists at the A1 Adenosine Receptor

N6-Substituted 9-methyladenines are potent antagonists of the activation of A1 adenosine receptors.The present study assessed the effect of N6 and N-9-substituents on the binding of adenines to the A1 and A2 receptors, respectively, of rat brain cortex and striatum and also on the antagonism of the A2 receptor mediated stimulation of the adenylate cyclase of PC12 cells by N-ethyladenosine-5'-uronamide.The potency ranking of 9-substituted adenines varied directly with the hydrophobicity of the substituent: cyclopentyl > phenyl > tetrahydrofuryl > ethyl > methyl > 2-hydroxyethyl.The 9-substituted adenines showed little selectivity for either receptor and the R enantiomer of N6-(1-phenyl-2-propyl)-9-methyladenine was only 4-fold more potent than the S enantiomer at the A1 receptor.An N6-cyclopentyl substituent increased potency at the A1 receptor and decreased potency at the A2 receptor, resulting in selectivity for the A1 receptor of up to 39-fold.The N6-cyclopentyl group completely overshadowed the effect of the hydrophobicity of the 9-substituent.A 2-chloro substituent did not alter the potency of an N6-substituted 9-methyladenine.