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

Base Information

• Chemical Name: 1-tert-butyl-3-(naphthalen-1-ylmethyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine
• CAS No.: 221244-14-0
• Molecular Formula: C₂₀H₂₁N₅
• Molecular Weight: 331.42
• UNII: 75BNB373NL
• ChEMBL ID: CHEMBL573578
• DSSTox Substance ID: DTXSID30408954
• Nikkaji Number: J1.461.158D
• Pharos Ligand ID: AFCJ95Q3AR7F
• Wikidata: Q27088429
• Mol file: 221244-14-0.mol

Synonyms:4-amino-1-tert-butyl-3-(1'-naphthylmethyl)pyrazolo(3,4-d)pyrimidine;4-amino-tBuNMPP

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

Chemical Property:

• Appearance/Colour: White cyrstalline solid
• Vapor Pressure: 5.79E-12mmHg at 25°C
• Melting Point: 175-176 °C
• Refractive Index: 1.675
• Boiling Point: 545.7 °C at 760 mmHg
• PKA: 4.50±0.30(Predicted)
• Flash Point: 283.8 °C
• PSA: 69.62000
• Density: 1.25 g/cm³
• LogP: 4.48870
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), Methanol (Slightly, Heated)
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 331.17969569
• Heavy Atom Count: 25
• Complexity: 462

Purity/Quality:

97% ^*data from raw suppliers

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)N1C2=NC=NC(=C2C(=N1)CC3=CC=CC4=CC=CC=C43)N
• Description: 1-NM-PP1 is a cell permeable inhibitor of kinases that have been mutated, by a single base substitution, to become ‘analog sensitive’ (as), as compared to the wild-type kinase. 1-NM-PP1 was first developed to optimally inhibit v-Src-as1, with an I338G substitution, preferentially over v-Src (IC50 = 4.2 nM versus 28 μM, respectively). The homologous mutation in other kinases generated similar analog sensitivity (e.g., IC50 = 3.2 nM for c-Fyn-as1 versus 1.0 μM for c-Fyn; 5.0 nM for Cdk2-as1 versus 29 μM for Cdk2; 8.0 nM for CAMKII-as1 versus 24 μM for CAMKII). This approach has been used to elucidate functions of several kinases in both mammalian and yeast systems.
• Uses: A highly potent (IC50=4.3 nM) and uniquely specific tyrosine kinase inhibitor of a rationally engineered v-Src tyrosine kinase

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

There total 9 articles about 1-tert-butyl-3-(naphthalen-1-ylmethyl)-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: 50.0%

formamide (77287-34-4,77287-35-5,60100-09-6) + 5-amino-1-tert-butyl-3-naphthalen-1-ylmethyl-1H-pyrazole-4-carbonitrile (221243-77-2) → 1-tert-butyl-3-(naphthalen-1-ylmethyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (221244-14-0)

Guidance literature:

at 150 ℃;

DOI:10.1039/c6md00675b

Reference yield: 18.0%

tertbutylhydrazine hydrochloride (7400-27-3) + formamide (77287-34-4,77287-35-5,60100-09-6) + 2-(1-methoxy-2-naphthalen-1-ylethylidene)malononitrile (221243-13-6) → 1-tert-butyl-3-(naphthalen-1-ylmethyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (221244-14-0)

Guidance literature:

tertbutylhydrazine hydrochloride; 2-(1-methoxy-2-naphthalen-1-ylethylidene)malononitrile; With triethylamine; In ethanol; for 3.5h; Reflux;

formamide; Reflux;

Reference yield:

naphthalen-1-yl-acetyl chloride (5121-00-6) → 1-tert-butyl-3-(naphthalen-1-ylmethyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (221244-14-0)

Guidance literature:

Multi-step reaction with 4 steps

1: NaH / tetrahydrofuran / 0.5 h / Ambient temperature

2: aq. NaHCO₃ / dioxane / 1 h / 80 °C

3: Et₃N / ethanol / 1 h / Heating

4: 12 h / 180 °C

With sodium hydride; sodium hydrogencarbonate; triethylamine; In tetrahydrofuran; 1,4-dioxane; ethanol;

DOI:10.1021/ja983267v

upstream raw materials:

formamide

5-amino-1-tert-butyl-3-naphthalen-1-ylmethyl-1H-pyrazole-4-carbonitrile

naphthalen-1-yl-acetyl chloride

naphth-1-yl acetic acid