1-Phenyl-1h-pyrazolo[3,4-d]pyrimidin-4-amine

Base Information

• Chemical Name: 1-Phenyl-1h-pyrazolo[3,4-d]pyrimidin-4-amine
• CAS No.: 5334-30-5
• Molecular Formula: C11H9N5
• Molecular Weight: 211.226
• Hs Code.: 29335995
• European Community (EC) Number: 310-193-6,808-056-5
• NSC Number: 1401
• DSSTox Substance ID: DTXSID20274448
• Nikkaji Number: J331.960A
• Wikidata: Q27088431
• ChEMBL ID: CHEMBL65063
• Mol file: 5334-30-5.mol

Synonyms:5334-30-5;1-phenyl-1h-pyrazolo[3,4-d]pyrimidin-4-amine;4-Amino-1-phenylpyrazolo[3,4-d]pyrimidine;PP 3;pp3;1-phenylpyrazolo[3,4-d]pyrimidin-4-amine;SBB028425;CHEMBL65063;1-Phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine;4-Amino-1-phenylpyrazolo(3,4-e)pyrimidine;4-AMINO-1-PHENYL-1H-PYRAZOLO[3,4-D]PYRIMIDINE;1H-Pyrazolo[3,4-d]pyrimidine, 4-amino-1-phenyl-;NSC 1401;NSC1401;D04XNJ;cid_4879;Oprea1_329529;Oprea1_457349;MLS000054252;GTPL6029;SCHEMBL2278510;CHEBI:92303;DTXSID20274448;HMS2502N08;HMS3229K03;NSC-1401;BDBM50013720;HB1336;HSCI1_000188;MFCD00022901;STL356148;AKOS000536351;CCG-206781;ES-0020;NCGC00037167-02;SMR000065878;HY-108484;CS-0028960;FT-0617437;T71017;1-Phenyl-1H-pyrazolo[3,4-d]pyrimidine-4-amine;EN300-1644893;1-Phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine #;BRD-K16977723-001-01-0;Q27088431;Z56801548;1345-16-0

Chemical Property of 1-Phenyl-1h-pyrazolo[3,4-d]pyrimidin-4-amine

Chemical Property:

• Appearance/Colour: Whit to Off-White Solid
• Vapor Pressure: 1.74E-05mmHg at 25°C
• Melting Point: 214-217 °C
• Refractive Index: 1.77
• Boiling Point: 364 °C at 760 mmHg
• Flash Point: 173.9 °C
• PSA: 69.62000
• Density: 1.44 g/cm³
• LogP: 1.97890
• Storage Temp.: -20°C
• Solubility.: DMF, DMSO, Hot methanol
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 211.08579531
• Heavy Atom Count: 16
• Complexity: 241

Purity/Quality:

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

PP3 ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)N2C3=NC=NC(=C3C=N2)N
• Uses: Intermediate in the preparation of various enzymatic inhibitors 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. Several small molecule inhibitors of this signaling pathway have been developed as a therapeuptic strategy to abate abnormal Src kinase activity. PP3 is an inactive analog of the Src tyrosine kinase inhibitors PP1 and PP2 . At concentrations as high as 10 μM, it does not prevent proliferation mediated by a stem cell factor/mast cell growth factor in hematopoietic and cancer cell lines.[Cayman Chemical]

Technology Process of 1-Phenyl-1h-pyrazolo[3,4-d]pyrimidin-4-amine

There total 8 articles about 1-Phenyl-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: 80.0%

5-Amino-4-cyano-1-phenylpyrazole (5334-43-0) + formamide (77287-34-4,77287-35-5,60100-09-6) → 1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine (5334-30-5)

Guidance literature:

for 2h; Reflux;

DOI:10.3906/kim-1303-20

Reference yield: 70.0%

ethyl N-(4-cyano-1-phenyl-1H-pyrazol-5-yl)formimidate (62564-59-4) → 1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine (5334-30-5)

Guidance literature:

With ammonia; acetic acid; In ethanol; for 6h; Reflux;

DOI:10.1007/s00044-013-0742-x

Reference yield: 16.01%

iodobenzene (591-50-4) + 4-Aminopyrazolo<3,4-d>pyrimidin (2380-63-4) → 1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine (5334-30-5)

Guidance literature:

With copper(l) iodide; potassium carbonate; In N,N-dimethyl-formamide; at 140 ℃; for 24h;

upstream raw materials:

5-Amino-4-cyano-1-phenylpyrazole

formamide

4-chloro-1-(phenyl)-1H-pyrazolo[3,4-d]pyrimidine

phenylhydrazine

Downstream raw materials:

6-cyano-7-imino-5-ethyl-N¹-phenyl-1, 7-dihydropyrazolo[3', 4':4, 5]pyrimido[1, 6-a]pyrimidine

6-cyano-7-imino-N¹-phenyl-1,7-dihydropyrazolo[3',4':4,5]pyrimido[1,6-a]pyrimidine

C₂₅H₂₃N₇O₂

C₂₆H₂₆N₆O

Refernces

• 1、 Cyr, Patrick,Joseph-Valcin, Eve-Marline,Boissarie, Patrick,Simoneau, Bruno,Marinier, Anne. "Copper-Catalyzed N1 Coupling of 3-Aminoindazoles and Related Aminoazoles with Aryl Bromides". supporting information. . Retrieved 2021/12/02.
• 2、 Rahmouni, Ameur,Romdhane, Anis,Ben Said, Abderrahim,Majouli, Kaouther,Ben Jannet, Hichem. "Synthesis of new pyrazole and antibacterial pyrazolopyrimidine derivatives". . p. 210 - 221. Retrieved 2014/04/03.