1-(tert-Butyl)-3-(p-tolyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Base Information

• Chemical Name: 1-(tert-Butyl)-3-(p-tolyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine
• CAS No.: 172889-26-8
• Molecular Formula: C16H19N5
• Molecular Weight: 281.36
• Hs Code.: 2933990090
• UNII: SA2ND7EHY4
• DSSTox Substance ID: DTXSID60274306
• Nikkaji Number: J704.781I
• Wikidata: Q27088427
• Pharos Ligand ID: L9GZXGYTYAJ6
• Metabolomics Workbench ID: 146437
• ChEMBL ID: CHEMBL306380
• Mol file: 172889-26-8.mol

Synonyms:172889-26-8;PP1;PP 1;1-(tert-Butyl)-3-(p-tolyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine;PYRAZOLOPYRIMIDINE 1;PP-1;SA2ND7EHY4;PP-1 (enzyme inhibitor);1-tert-butyl-3-(4-methylphenyl)pyrazolo[3,4-d]pyrimidin-4-amine;1-tert-butyl-3-(4-methylphenyl)-1h-pyrazolo[3,4-d]pyrimidin-4-amine;CHEMBL306380;1-ter-butyl-3-p-tolyl-1h-pyrazolo[3,4-d]pyrimidin-4-ylamine;1-tert-butyl-3-p-tolyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine;AGL 1872;AGL-1872;EI-275;1-(1,1-DIMETHYLETHYL)-1-(4-METHYLPHENYL)-1H-PYRAZOLO[3,4-D]PYRIMIDIN-4-AMINE;1-(tert-butyl)-3-(4-methylphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine;4-AMINO-1-TERT-BUTYL-3-(4-METHYLPHENYL)PYRAZOLO[3,4-D]PYRIMIDINE;1-(1,1-Dimethylethyl)-3-(4-methylphenyl)-1H-pyrazolo(3,4-d)pyrimidin-4-amine;1H-Pyrazolo(3,4-d)pyrimidin-4-amine, 1-(1,1-dimethylethyl)-3-(4-methylphenyl)-;4fev;C16H19N5;1H-Pyrazolo[3,4-d]pyrimidin-4-amine,1-(1,1-dimethylethyl)-3-(4-methylphenyl)-;MFCD01076570;Kinome_2004;BiomolKI_000024;UNII-SA2ND7EHY4;BiomolKI2_000032;cid_1400;CBiol_001915;Oprea1_734810;BSPBio_001034;KBioGR_000374;KBioSS_000374;ksc-8-189;MLS000326642;SCHEMBL407934;BMK1-C12;GTPL8836;BCBcMAP01_000234;BDBM25116;KBio2_000374;KBio2_002942;KBio2_005510;KBio3_000727;KBio3_000728;DTXSID60274306;EX-A344;Bio1_000201;Bio1_000690;Bio1_001179;Bio2_000357;Bio2_000837;HMS1362D15;HMS1792D15;HMS1990D15;HMS2191A04;HMS3267F12;HMS3403D15;HMS3412M08;HMS3652F20;HMS3673K19;HMS3676M08;HMS3742E09;KUC105857N;AMY14210;BCP07604;EI 275;HB1334;s7060;AKOS005080619;PP1, >=98% (HPLC);CCG-100628;CS-1662;DB01809;MB01692;IDI1_002112;QTL1_000067;NCGC00163376-01;NCGC00163376-02;NCGC00163376-03;NCGC00163376-14;12L-341S;AC-32819;HY-13804;SMR000179220;FT-0661640;SW220208-1;VU0205191-1;M02255;Src Inhibitor, PP1 - CAS 172889-26-8;J-010857;BRD-K47598052-001-04-2;BRD-K47598052-001-06-7;Q27088427;1-tert-butyl-3-(p-tolyl)pyrazolo[3,4-d]pyrimidin-4-amine;1-tert-butyl-3-(4-methylphenyl)pyrazolo[4,5-e]pyrimidin-4-amine;1-tert-butyl-3-(p-tolyl)-1h-pyrazolo[3,4-d]pyrimidin-4-amine;4-Amino-5-(methylphenyl)-7-(tert.butyl)pyrazolo-(3,4-d)pyrimidine

Chemical Property of 1-(tert-Butyl)-3-(p-tolyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Chemical Property:

• Appearance/Colour: Off-white to grey solid
• Vapor Pressure: 2.49E-09mmHg at 25°C
• Melting Point: 205-207 °C
• Refractive Index: 1.652
• Boiling Point: 478.8 °C at 760 mmHg
• Flash Point: 243.4 °C
• PSA: 69.62000
• Density: 1.23 g/cm³
• LogP: 3.72010
• Storage Temp.: Desiccate at +4°C
• Solubility.: DMSO: >20mg/mL
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 281.16404563
• Heavy Atom Count: 21
• Complexity: 358

Purity/Quality:

97% ^*data from raw suppliers

4-Amino-1-tert-butyl-3-(4-methylphenyl)pyrazolo[3,4-d]pyrimidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)C2=NN(C3=NC=NC(=C23)N)C(C)(C)C
• Description: PP1 (172889-26-8) is a potent and selective inhibitor of Src family tyrosine kinases. IC50=5 nM (p65lck), IC50=6 nM(P59fynT), IC50=170 nM (p60src). Cell permeable.
• Uses: A highly potent and uniquely specific tyrosine kinase inhibitor of a rationally engineered v-Src tyrosine kinase PP1 has been used as: an inhibitor of sarcoma (Src) family kinases (SFK) like hematopoietic cell kinase (hck) and fyn a selective Src tyrosine kinase inhibitor in hippocampal neuronal cultures to test its effect on neurite growth a Src-kinase blocker to test its effect on brimonidine (BMD)-induced phosphorylation in extracellular signal-activated kinases(ERK1/2)

Technology Process of 1-(tert-Butyl)-3-(p-tolyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

There total 7 articles about 1-(tert-Butyl)-3-(p-tolyl)-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: 81.0%

3-bromo-1-(tert-butyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (862728-61-8) + 4-methylphenylboronic acid (5720-05-8) → 1-(t-butyl)-3-(4-methylphenyl)-4-aminopyrazolo[3,4-d]pyrimidine (172889-26-8)

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) → 1-(t-butyl)-3-(4-methylphenyl)-4-aminopyrazolo[3,4-d]pyrimidine (172889-26-8)

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) → 1-(t-butyl)-3-(4-methylphenyl)-4-aminopyrazolo[3,4-d]pyrimidine (172889-26-8)

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:

formamide

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-methylphenylboronic acid