2-Chloro-6(methylamino)purine

Base Information

• Chemical Name: 2-Chloro-6(methylamino)purine
• CAS No.: 82499-02-3
• Molecular Formula: C6H6ClN5
• Molecular Weight: 183.6
• Hs Code.: 2933990090
• ChEMBL ID: CHEMBL446449
• DSSTox Substance ID: DTXSID00404544
• Nikkaji Number: J407.769E
• NSC Number: 15416
• Wikidata: Q82208806
• Mol file: 82499-02-3.mol

Synonyms:2-Chloro-6(methylamino)purine;82499-02-3;2-CHLORO-N-METHYL-9H-PURIN-6-AMINE;2-chloro-N-methyl-7H-purin-6-amine;CHEMBL446449;2-chloranyl-~{N}-methyl-9~{H}-purin-6-amine;OYN;2-CHLORO-6-(N-METHYLAMINO)-9H-PURINE;2-chloro-6-methylaminopurine;SCHEMBL130696;DTXSID00404544;RIAVUEFUPHOGJY-UHFFFAOYSA-N;2-Chloro-6-methylamino-9H-purine;NSC15416;BDBM50208873;MFCD08272066;NSC-15416;2-Chloro-6(methylamino)purine, 97%;AKOS006283488;AKOS015894684;AB44277;PD180398;WS-02650;C90626;EN300-698652

Chemical Property of 2-Chloro-6(methylamino)purine

Chemical Property:

• Vapor Pressure: 0.00343mmHg at 25°C
• Melting Point: >300oC(lit.)
• Boiling Point: 282.1°C at 760 mmHg
• Flash Point: 124.4°C
• PSA: 66.49000
• Density: 1.76g/cm³
• LogP: 1.12100
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 183.0311729
• Heavy Atom Count: 12
• Complexity: 166

Purity/Quality:

98%,99%, ^*data from raw suppliers

2-Chloro-6(methylamino)purine 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-43-41-37/38
• Safety Statements: 36/37-39-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CNC1=NC(=NC2=C1NC=N2)Cl

Technology Process of 2-Chloro-6(methylamino)purine

There total 6 articles about 2-Chloro-6(methylamino)purine 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: 93.5%

2,6 dichloropurine (5451-40-1) + methylamine (74-89-5) → 2-chloro-6-(N-methylamino)-9H-purine (82499-02-3)

Guidance literature:

In water; at 100 ℃; for 1h;

DOI:10.1021/jm990249v

Reference yield:

methylamine (74-89-5) + 2,6-dichloro-7H-purine (5451-40-1) → 2-chloro-N-methylpurin-6-amine (82499-02-3)

Guidance literature:

With water;

DOI:10.1021/ja01535a040

Reference yield:

2-chloro-N-(2,2,2-trifluoroethyl)-9H-purine-6-amine → 2-chloro-6-(N-methylamino)-9H-purine (82499-02-3)

Guidance literature:

Multi-step reaction with 2 steps

1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; XPhos; potassium tert-butylate / tert-butyl alcohol / 16 h / 100 °C / Inert atmosphere

2: isopropyl alcohol; tetrahydrofuran / 4 h / 80 °C

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; potassium tert-butylate; XPhos; In tetrahydrofuran; isopropyl alcohol; tert-butyl alcohol; 1: |Buchwald-Hartwig Coupling;

DOI:10.1021/acs.jmedchem.0c01017

upstream raw materials:

methylamine

2,6-dichloro-7H-purine

2,6 dichloropurine

Downstream raw materials:

N²-butyl-N⁶-methyl-7(9)H-purine-2,6-diyldiamine

2-[2-(2-chloro-6-methylamino-purin-9-yl)-ethyl]-2-ethoxycarbonyl-malonic acid diethyl ester

Refernces

• 1、 Singh, Baljinder,Diaz-Gonzalez, Rosario,Ceballos-Perez, Gloria,Rojas-Barros, Domingo I.,Gunaganti, Naresh,Gillingwater, Kirsten,Martinez-Martinez, Maria Santos,Manzano, Pilar,Navarro, Miguel,Pollastri, Michael P.. "Medicinal Chemistry Optimization of a Diaminopurine Chemotype: Toward a Lead for Trypanosoma brucei Inhibitors". . p. 9912 - 9927. Retrieved 2020/10/19.
• 2、 Goswami, Manibarsha,Wilke, Kaelyn E.,Carlson, Erin E.. "Rational Design of Selective Adenine-Based Scaffolds for Inactivation of Bacterial Histidine Kinases". supporting information. p. 8170 - 8182. Retrieved 2017/10/18.