tert-butyl N-tert-butoxycarbonyl-N-[5-(4-isopropylsulfonylphenyl)-3-(2-trimethylsilylethynyl)pyrazin-2-yl]carbamate

Base Information

• Chemical Name: tert-butyl N-tert-butoxycarbonyl-N-[5-(4-isopropylsulfonylphenyl)-3-(2-trimethylsilylethynyl)pyrazin-2-yl]carbamate
• CAS No.: 1350351-56-2
• Molecular Formula: C₂₈H₃₉N₃O₆SSi
• Molecular Weight: 573.786
• Mol file: 1350351-56-2.mol

Synonyms:tert-butyl N-tert-butoxycarbonyl-N-[5-(4-isopropylsulfonylphenyl)-3-(2-trimethylsilylethynyl)pyrazin-2-yl]carbamate

Chemical Property of tert-butyl N-tert-butoxycarbonyl-N-[5-(4-isopropylsulfonylphenyl)-3-(2-trimethylsilylethynyl)pyrazin-2-yl]carbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl N-tert-butoxycarbonyl-N-[5-(4-isopropylsulfonylphenyl)-3-(2-trimethylsilylethynyl)pyrazin-2-yl]carbamate

There total 4 articles about tert-butyl N-tert-butoxycarbonyl-N-[5-(4-isopropylsulfonylphenyl)-3-(2-trimethylsilylethynyl)pyrazin-2-yl]carbamate 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: 100.0%

di-tert-butyl dicarbonate (24424-99-5) + 5-(4-isopropylsulfonylphenyl)-3-(2-trimethylsilylethynyl)pyrazin-2-amine (1350351-55-1) → tert-butyl N-tert-butoxycarbonyl-N-[5-(4-isopropylsulfonylphenyl)-3-(2-trimethylsilylethynyl)pyrazin-2-yl]carbamate (1350351-56-2)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃; for 18h;

DOI:10.1021/acs.jmedchem.9b00426

Reference yield:

4-(isopropylsulfonyl)phenylboronic acid (850567-98-5) → tert-butyl N-tert-butoxycarbonyl-N-[5-(4-isopropylsulfonylphenyl)-3-(2-trimethylsilylethynyl)pyrazin-2-yl]carbamate (1350351-56-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: potassium phosphate / bis(tri-t-butylphosphine)palladium⁽⁰⁾ / acetonitrile; water / 1 h / 60 °C

2.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 2 h / 20 °C

3.1: triethylamine / tetrakis(triphenylphosphine) palladium⁽⁰⁾; copper(l) iodide / N,N-dimethyl-formamide / 3 h / 0 °C / Cooling with ice

3.2: 2.17 h / 20 °C / Cooling with ice

4.1: dmap; triethylamine / dichloromethane / 16 h / 20 °C

With dmap; potassium phosphate; N-Bromosuccinimide; triethylamine; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; bis(tri-t-butylphosphine)palladium⁽⁰⁾; In dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

Reference yield:

5-(4-(isopropylsulfonyl)phenyl)pyrazin-2-amine (1349151-81-0) → tert-butyl N-tert-butoxycarbonyl-N-[5-(4-isopropylsulfonylphenyl)-3-(2-trimethylsilylethynyl)pyrazin-2-yl]carbamate (1350351-56-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 2 h / 20 °C

2.1: triethylamine / tetrakis(triphenylphosphine) palladium⁽⁰⁾; copper(l) iodide / N,N-dimethyl-formamide / 3 h / 0 °C / Cooling with ice

2.2: 2.17 h / 20 °C / Cooling with ice

3.1: dmap; triethylamine / dichloromethane / 16 h / 20 °C

With dmap; N-Bromosuccinimide; triethylamine; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In dichloromethane; N,N-dimethyl-formamide;

upstream raw materials:

di-tert-butyl dicarbonate

5-(4-isopropylsulfonylphenyl)-3-(2-trimethylsilylethynyl)pyrazin-2-amine

4-(isopropylsulfonyl)phenylboronic acid

5-(4-(isopropylsulfonyl)phenyl)pyrazin-2-amine

Downstream raw materials:

tert-butyl N-(3-ethynyl-5-(4-(isopropylsulfonyl)phenyl)pyrazin-2-yl)N-tertbutoxycarbonyl-carbamate ?

di-tert-butyl 3-((3-((tert-butoxycarbonyl(methyl)amino)methyl)phenyl)ethynyl)-5-(4-(isopropylsulfonyl)phenyl)pyrazin-2-yliminodicarbonate

tert-butyl tert-butoxycarbonyl(3-((4-(2-((tert-butoxycarbonyl)amino)-1-hydroxyethyl)phenyl)ethynyl)-5-(4-(isopropylsulfonyl)phenyl)pyrazin-2-yl)carbamate

3-[2-[3-amino-6-(4-isopropylsulfonylphenyl)pyrazin-2-yl]ethynyl]benzamide