6-(cyclohexylmethoxy)-9H-purin-2-amine

Base Information

• Chemical Name: 6-(cyclohexylmethoxy)-9H-purin-2-amine
• CAS No.: 161058-83-9
• Molecular Formula: C12H17N5O
• Molecular Weight: 247.3
• Hs Code.: 2933990090
• European Community (EC) Number: 633-908-6
• NSC Number: 707619
• UNII: 884MN6AR44
• Nikkaji Number: J814.488E
• Wikidata: Q27093409
• Metabolomics Workbench ID: 146994
• ChEMBL ID: CHEMBL269881
• Mol file: 161058-83-9.mol

Synonyms:NU2058;O(6)-cyclohexylmethylguanine

Chemical Property of 6-(cyclohexylmethoxy)-9H-purin-2-amine

Chemical Property:

• Vapor Pressure: 1.76E-13mmHg at 25°C
• Melting Point: 199°C(lit.)
• Boiling Point: 580.8oC at 760 mmHg
• PKA: 7.36±0.20(Predicted)
• Flash Point: 305oC
• PSA: 89.71000
• Density: 1.52±0.1 g/cm3(Predicted)
• LogP: 2.47540
• Storage Temp.: 2-8°C
• Solubility.: DMSO: 22 mg/mL
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 247.14331018
• Heavy Atom Count: 18
• Complexity: 271

Purity/Quality:

99% ^*data from raw suppliers

NU 2058 ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CCC(CC1)COC2=NC(=NC3=C2NC=N3)N
• Description: NU 2058 is an inhibitor of cyclin-dependent kinase 1 (Cdk1) and Cdk2 (IC50s = 7.0 and 17 μM, respectively). Increased Cdk activity is often associated with human tumors, and inhibitors of Cdks, including NU 2058, can arrest cell cycling in cancer cells in vitro.
• Uses: NU 2058 is an intermediate of NU 6140 (N925295), a cyclin-dependant kinase 2 inhibitor which demonstrates 10-36 fold selectivity against Cdk2-cyclin A. This selectivity induces cell-cycle arrest at the G2-M phase and potentiates the apoptotic effect of pacitaxel.

Technology Process of 6-(cyclohexylmethoxy)-9H-purin-2-amine

There total 4 articles about 6-(cyclohexylmethoxy)-9H-purin-2-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: 72.0%

2-Amino-6-chloropurin (10310-21-1) + cyclohexylmethyl alcohol (100-49-2) → NU 2058 (161058-83-9)

Guidance literature:

With sodium; Heating;

DOI:10.1021/jm000961o

Reference yield: 51.0%

1-(2-amino-9H-purin-6-yl)-4-aza-1-azoniabicyclo[2.2.2]octane chloride + cyclohexylmethyl alcohol (100-49-2) → NU 2058 (161058-83-9)

Guidance literature:

With sodium hydride; In dimethyl sulfoxide; 1.) r.t., 1 h, 2.) r.t., 72 h;

DOI:10.1039/a608207f

Reference yield:

2-Amino-6-chloropurin (10310-21-1) → NU 2058 (161058-83-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / dimethylsulfoxide / 12 h / Ambient temperature

2: 51 percent / NaH / dimethylsulfoxide / 1.) r.t., 1 h, 2.) r.t., 72 h

With sodium hydride; In dimethyl sulfoxide;

DOI:10.1039/a608207f

upstream raw materials:

cyclohexylmethyl alcohol

2-Amino-6-chloropurin

Downstream raw materials:

6-(cyclohexylmethoxy)-2-fluoro-9H-purine

2-amino-9-benzyl-6-cyclohexylmethoxy-9H-purine