1-tert-butyl-3-(4-chlorophenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Base Information

• Chemical Name: 1-tert-butyl-3-(4-chlorophenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine
• CAS No.: 172889-27-9
• Molecular Formula: C₁₅H₁₆ClN₅
• Molecular Weight: 301.779
• Hs Code.: 2933990090
• European Community (EC) Number: 878-892-3
• UNII: PK8JPC58XB
• DSSTox Substance ID: DTXSID60274447
• Nikkaji Number: J704.782G
• Wikipedia: PP2_(kinase_inhibitor)
• Wikidata: Q7120082
• Pharos Ligand ID: L3W78VVYQB1H
• ChEMBL ID: CHEMBL406845
• Mol file: 172889-27-9.mol

Synonyms:4-amino-5-(4-chlorophenyl)-7-(t-butyl)pyrazolo(3,4-d)pyrimidine;AG 1879;AG1879;PP2 cpd;Src family kinase inhibitor PP2

Chemical Property of 1-tert-butyl-3-(4-chlorophenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Chemical Property:

• Appearance/Colour: White solid
• Vapor Pressure: 6.98E-10mmHg at 25°C
• Melting Point: 214-216oC
• Refractive Index: 1.676
• Boiling Point: 493.5 °C at 760 mmHg
• PKA: 3.96±0.30(Predicted)
• Flash Point: 252.3 °C
• PSA: 69.62000
• Density: 1.35 g/cm³
• LogP: 4.06510
• Storage Temp.: Desiccate at +4°C
• Solubility.: Soluble in DMSO (up to 25 mg/ml) or in Ethanol (up to 3 mg/ml with warming).
• XLogP3: 3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 301.1094232
• Heavy Atom Count: 21
• Complexity: 364

Purity/Quality:

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

PP2 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25
• Safety Statements: 45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)N1C2=NC=NC(=C2C(=N1)C3=CC=C(C=C3)Cl)N
• Description: The Src family of non-receptor tyrosine kinases regulate cell adhesion, growth, and differentiation through activation of multiple intracellular signaling pathways. Normally inactive, Src kinases are transiently activated during mitosis and constitutively activated by abnormal mutations. PP2 is a potent, reversible, ATP-competitive, and selective inhibitor of the Src family of protein tyrosine kinases. It inhibits p56lck (IC50 = 4 nM), p59fynT (IC50 = 5 nM), Hck (IC50 = 5 nM), and Src (IC50 = 100 nM). PP2 does not significantly affect the activity of EGFR kinase (IC50 = 480 nM), JAK2 (IC50 > 50 μM), or ZAP-70 (IC50 > 100 μM). PP2 inhibits the activation of focal adhesion kinase as well as its phosphorylation at Tyr577. PP2 also inhibits anti-CD3-stimulated tyrosine phosphorylation of human T-cells with an IC50 value of 600 nM.
• Uses: PP2 has been used:to analyze the effects of Src/focal adhesion kinase (FAK) signaling on IQ domain GTPase-activating protein 1 (IQGAP1)-mediated anoikis resistancefor Src inhibition to study its effect on epidermal growth factor receptor (EGFR) and nuclear factor erythroid 2-related factor 2 (Nrf2) phosphorylation in non-small cell lung cancer (NSCLC) cellsfor pharmacological inhibition of SRC in MDA-MB-231 breast cancer cells

Technology Process of 1-tert-butyl-3-(4-chlorophenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

There total 3 articles about 1-tert-butyl-3-(4-chlorophenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-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: 85.0%

3-bromo-1-(tert-butyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (862728-61-8) + 4-Chlorophenylboronic acid (1679-18-1) → PP2 (172889-27-9)

Guidance literature:

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; caesium carbonate; 1,3,5,7-tetramethyl-8-phenyl-2,4,6-trioxa-8-phosphatricyclo[3.3.1.13,7]decane; In toluene; at 100 ℃; for 0.5h; Microwave irradiation; Inert atmosphere;

DOI:10.1016/j.tetlet.2011.08.103

Reference yield:

5-amino-1-(tert-butyl)-1H-pyrazole-4-carbonitrile (158001-28-6) → PP2 (172889-27-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 0.5 h / 180 °C / Microwave irradiation; Inert atmosphere

2: bromine / water / 2 h / 20 - 100 °C

3: tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; caesium carbonate; 1,3,5,7-tetramethyl-8-phenyl-2,4,6-trioxa-8-phosphatricyclo[3.3.1.13,7]decane / toluene / 0.5 h / 100 °C / Microwave irradiation; Inert atmosphere

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; bromine; caesium carbonate; 1,3,5,7-tetramethyl-8-phenyl-2,4,6-trioxa-8-phosphatricyclo[3.3.1.13,7]decane; In water; toluene; 3: Suzuki coupling;

DOI:10.1016/j.tetlet.2011.08.103

Reference yield:

1-(1,1-dimethylethyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (862728-60-7) → PP2 (172889-27-9)

Guidance literature:

Multi-step reaction with 2 steps

1: bromine / water / 2 h / 20 - 100 °C

2: tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; caesium carbonate; 1,3,5,7-tetramethyl-8-phenyl-2,4,6-trioxa-8-phosphatricyclo[3.3.1.13,7]decane / toluene / 0.5 h / 100 °C / Microwave irradiation; Inert atmosphere

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; bromine; caesium carbonate; 1,3,5,7-tetramethyl-8-phenyl-2,4,6-trioxa-8-phosphatricyclo[3.3.1.13,7]decane; In water; toluene; 2: Suzuki coupling;

DOI:10.1016/j.tetlet.2011.08.103

upstream raw materials:

1-(1,1-dimethylethyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

3-bromo-1-(tert-butyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

4-Chlorophenylboronic acid

5-amino-1-(tert-butyl)-1H-pyrazole-4-carbonitrile

Refernces