3-[[6-(3-Aminophenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]phenol

Base Information

• Chemical Name: 3-[[6-(3-Aminophenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]phenol
• CAS No.: 601514-19-6
• Molecular Formula: C18H14N4O2
• Molecular Weight: 318.335
• European Community (EC) Number: 637-358-8
• DSSTox Substance ID: DTXSID00429550
• Nikkaji Number: J1.924.908E
• Wikidata: Q27089039
• Pharos Ligand ID: FG5BR2HFQ4X2
• ChEMBL ID: CHEMBL405759
• Mol file: 601514-19-6.mol

Synonyms:TWS 119;TWS-119;TWS119

Chemical Property of 3-[[6-(3-Aminophenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]phenol

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 249 °C
• Boiling Point: 646.028°C at 760 mmHg
• PKA: 8.99±0.10(Predicted)
• Flash Point: 344.505°C
• PSA: 97.05000
• Density: 1.42
• LogP: 4.28620
• Storage Temp.: Desiccate at +4°C
• Solubility.: insoluble in H2O; insoluble in EtOH; ≥15.9 mg/mL in DMSO
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 318.11167570
• Heavy Atom Count: 24
• Complexity: 424

Purity/Quality:

97% ^*data from raw suppliers

TWS 119 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC(=C1)N)C2=CC3=C(N2)N=CN=C3OC4=CC=CC(=C4)O
• Uses: Acts as an ARMS-selective inihibitor, through GSK3 (Glucose Synthase Kinase 3) inhibition. TWS119 has been used as glycogen synthase kinase-3β (GSK-3β) GSK3β inhibitor.

Technology Process of 3-[[6-(3-Aminophenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]phenol

There total 1 articles about 3-[[6-(3-Aminophenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]phenol 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: 80.0%

3-(4-(3-methoxyphenoxy)-7H-pyrrolo[2,3-d]pyrimidin-6-yl)aniline (1236291-88-5) → TWS 119 (601514-19-6)

Guidance literature:

With boron tribromide; In dichloromethane; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1016/j.tetlet.2010.05.032

Reference yield:

TWS 119 (601514-19-6) → C18H13FN4O4S

Guidance literature:

With fluorosulfonyl fluoride; triethylamine; In dimethyl sulfoxide; acetonitrile; at 20 ℃;

DOI:10.1021/jacs.7b12788

upstream raw materials:

3-(4-(3-methoxyphenoxy)-7H-pyrrolo[2,3-d]pyrimidin-6-yl)aniline