DAPIVIRINE,4-[[4-(2,4,6-TRIMETHYLPHENYL)AMINO]PYRIMIDIN-2-YL]AMINO]BENZONITRILE

Base Information

• Chemical Name: DAPIVIRINE,4-[[4-(2,4,6-TRIMETHYLPHENYL)AMINO]PYRIMIDIN-2-YL]AMINO]BENZONITRILE
• CAS No.: 244767-67-7
• Molecular Formula: C20H19N5
• Molecular Weight: 329.404
• Mol file: 244767-67-7.mol

Synonyms:4-[[4-[(2,4,6-Trimethylphenyl)amino]-2-pyrimidinyl]amino]benzonitrile;R 147681;TMC 120;TMC 120R147681;

Chemical Property of DAPIVIRINE,4-[[4-(2,4,6-TRIMETHYLPHENYL)AMINO]PYRIMIDIN-2-YL]AMINO]BENZONITRILE

Chemical Property:

• Vapor Pressure: 1.76E-12mmHg at 25°C
• Refractive Index: 1.648
• Boiling Point: 557.9 °C at 760 mmHg
• PKA: 4.74±0.10(Predicted)
• Flash Point: 291.2 °C
• PSA: 73.63000
• Density: 1.23 g/cm³
• LogP: 4.90668
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility.: DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

99%Min. ^*data from raw suppliers

Dapivirine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Non-nucleoside Reverse Transcriptase inhibitor. An antiviral agent. Non-nucleoside Reverse Transcriptase inhibitor. An antiviral agent

Technology Process of DAPIVIRINE,4-[[4-(2,4,6-TRIMETHYLPHENYL)AMINO]PYRIMIDIN-2-YL]AMINO]BENZONITRILE

There total 8 articles about DAPIVIRINE,4-[[4-(2,4,6-TRIMETHYLPHENYL)AMINO]PYRIMIDIN-2-YL]AMINO]BENZONITRILE 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: 96.0%

potassium cyanide + C19H19BrN4 → dapivirine (244767-67-7)

Guidance literature:

potassium cyanide; With acetic acid; In ethylene glycol; Sealed tube;

C₁₉H₁₉BrN₄; With P(t-Bu)3 Palladacycle Gen_. 3; potassium acetate; In 1,4-dioxane; water; at 60 ℃; for 16h; Sealed tube;

DOI:10.1039/c7sc03912c

Reference yield: 42.0%

2-chloro-N-mesitylpyrimidin-4-amine (244768-44-3) + 4-Aminobenzonitrile (873-74-5) → dapivirine (244767-67-7)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; ethanol; Reflux;

DOI:10.1016/j.bmc.2014.08.005

Reference yield:

4-Aminobenzonitrile (873-74-5) → dapivirine (244767-67-7)

Guidance literature:

Multi-step reaction with 3 steps

1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 20 °C

2: N-ethyl-N,N-diisopropylamine / tetrahydrofuran

3: palladium on activated charcoal; hydrogen

With palladium on activated charcoal; hydrogen; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran;

DOI:10.1016/j.bmcl.2013.06.091

upstream raw materials:

2,4,6-trimethylaniline

4-Aminobenzonitrile

4-(4-chloro-6-(mesitylamino)pyrimidin-2-ylamino)benzonitrile

4-(4,6-dichloropyrimidine-2-yl-amino)benzonitrile

Refernces

• 1、 Venkatraj, Muthusamy,Arin, Kevin K.,Heeres, Jan,Joossens, Jurgen,Diri, Bertrand,Lyssens, Sophie,Michiels, Johan,Cos, Paul,Lewi, Paul J.,Vanham, Guido,Maes, Louis,Van Der Veken, Pieter,Augustyns, Koen. "From human immunodeficiency virus non-nucleoside reverse transcriptase inhibitors to potent and selective antitrypanosomal compounds". . p. 5241 - 5248. Retrieved 2014/12/11.
• 2、 -. "Prodrugs of hiv replication inhibiting pyrimidines". . . Retrieved 2008/06/13.