N-Benzyl-2-Chloro-9-Methyl-9H-Purin-6-Amine

Base Information

• Chemical Name: N-Benzyl-2-Chloro-9-Methyl-9H-Purin-6-Amine
• CAS No.: 101622-53-1
• Molecular Formula: C13H12ClN5
• Molecular Weight: 273.725
• Hs Code.: 2933990090
• ChEMBL ID: CHEMBL133042
• DSSTox Substance ID: DTXSID20576959
• Nikkaji Number: J447.838J
• Wikidata: Q72454587
• Mol file: 101622-53-1.mol

Synonyms:N-Benzyl-2-Chloro-9-Methyl-9H-Purin-6-Amine;101622-53-1;CDK2-IN-13;N-BENZYL-2-CHLORO-9-METHYLPURIN-6-AMINE;CHEMBL133042;9H-Purin-6-amine, 2-chloro-9-methyl-N-(phenylmethyl)-;2-Chloro-9-methyl-6-(benzylamino)purine-d3;SCHEMBL8010398;DTXSID20576959;QNKNBVBQFILDGJ-UHFFFAOYSA-N;BEA62253;BDBM50056174;AKOS015839364;HY-W478102;NCGC00168488-01;MS-23887;CS-0554362;F97072;A898754;Benzyl-(2-chloro-9-methyl-9H-purin-6-yl)-amine

Chemical Property of N-Benzyl-2-Chloro-9-Methyl-9H-Purin-6-Amine

Chemical Property:

• Vapor Pressure: 4.77E-08mmHg at 25°C
• Boiling Point: 443.1°C at 760 mmHg
• Flash Point: 221.8°C
• PSA: 55.63000
• Density: 1.40±0.1 g/cm3 (20 ºC 760 Torr)
• LogP: 2.70180
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), DCM (Slightly), Ethyl Acetate (Slightly), Methanol (Sligh
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 273.0781231
• Heavy Atom Count: 19
• Complexity: 297

Purity/Quality:

98%min ^*data from raw suppliers

2-Chloro-9-methyl-6-(benzylamino)purine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C=NC2=C(N=C(N=C21)Cl)NCC3=CC=CC=C3
• Uses: 2-Chloro-9-methyl-6-(benzylamino)purine is an intermediate in the synthesis of Olomoucine (O567000), a purine derivative which inhibits cyclin-dependent kinases and induces G1 arrest.

Technology Process of N-Benzyl-2-Chloro-9-Methyl-9H-Purin-6-Amine

There total 9 articles about N-Benzyl-2-Chloro-9-Methyl-9H-Purin-6-Amine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.5%

N6-benzyl-2-chloroadenine (39639-47-9) + methyl iodide (74-88-4) → 2-chloro-6-benzylamino-9-methylpurine (101622-53-1)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 24h;

DOI:10.1002/(SICI)1521-4184(19996)332:6<187::AID-ARDP187>3.0.CO;2-D

Reference yield: 68.0%

2,6-dichloro-9-methyl-9H-purine (2382-10-7) + benzylamine (100-46-9) → 2-chloro-6-benzylamino-9-methylpurine (101622-53-1)

Guidance literature:

With triethylamine; In butan-1-ol; at 120 ℃; for 0.5h; Inert atmosphere; Microwave irradiation;

DOI:10.1021/ml3002083

Reference yield:

2,6 dichloropurine (5451-40-1) → 2-chloro-6-benzylamino-9-methylpurine (101622-53-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 80.5 percent / butan-1-ol / 5 h / 100 °C

2: 90.5 percent / NaH / dimethylformamide / 24 h / 20 °C

With sodium hydride; In N,N-dimethyl-formamide; butan-1-ol;

DOI:10.1002/(SICI)1521-4184(19996)332:6<187::AID-ARDP187>3.0.CO;2-D

upstream raw materials:

2,6-dichloro-9-methyl-9H-purine

benzylamine

N⁶-benzyl-2-chloroadenine

methyl iodide

Downstream raw materials:

(R)-6-(benzylamino)-2-[[(1-hydroxymethyl)propyl]amino]-9-methylpurine

2-(2-hydroxyisobutylamino)-6-benzylamino-9-methylpurine

olomoucine

Refernces

• 1、 -. "IMAGING AGENTS FOR NEURAL FLUX". Page/Page column 121. . Retrieved 2016/02/10.
• 2、 Liang, Mary,Tarr, Tyler B.,Bravo-Altamirano, Karla,Valdomir, Guillermo,Rensch, Gabriel,Swanson, Lauren,Destefino, Nicholas R.,Mazzarisi, Cara M.,Olszewski, Rachel A.,Wilson, Gabriela Mustata,Meriney, Stephen D.,Wipf, Peter. "Synthesis and biological evaluation of a selective N- and P/Q-Type calcium channel agonist". supporting information. p. 985 - 990. Retrieved 2013/02/23.