N-(tert-Butyl)-3-((2-chloro-5-methylpyrimidin-4-yl)amino)benzenesulfonamide

Base Information

• Chemical Name: N-(tert-Butyl)-3-((2-chloro-5-methylpyrimidin-4-yl)amino)benzenesulfonamide
• CAS No.: 936092-53-4
• Molecular Formula: C15H19ClN4O2S
• Molecular Weight: 354.86
• Hs Code.: 2935009090
• DSSTox Substance ID: DTXSID30694794
• Wikidata: Q72455053
• Mol file: 936092-53-4.mol

Synonyms:936092-53-4;N-(tert-Butyl)-3-((2-chloro-5-methylpyrimidin-4-yl)amino)benzenesulfonamide;N-tert-butyl-3-(2-chloro-5-methylpyrimidin-4-ylamino)benzenesulfonamide;N-TERT-BUTYL-3-[(2-CHLORO-5-METHYLPYRIMIDIN-4-YL)AMINO]BENZENESULFONAMIDE;SCHEMBL265954;AMY7183;DTXSID30694794;VINYOUWDZHOVFB-UHFFFAOYSA-N;AKOS037647203;SB58008;AS-72812;CS-0061358;W16891;A916584;N-t-butyl-3-(2-chloro-5-methyl-pyrimidin-4-ylamino)-benzenesulfon amide;N-tert-Butyl-3-(2-chloro-5-methyl-pyrimidin-4-ylamino)-benzenesulfonamide;3-((2-chloro-5-methyl-4-pyrimidinyl)amino)-n-(tert-butyl)benzenesulfonamide;N-tert-Butyl-3-[(2-chloro-5-methylpyrimidin-4-yl)amino]benzene-1-sulfonamide;N-tert-butyl-3-[(2-chloro-5-methyl-3,4-dihydropyrimidin-4-ylidene)amino]benzene-1-sulfonamide

Chemical Property of N-(tert-Butyl)-3-((2-chloro-5-methylpyrimidin-4-yl)amino)benzenesulfonamide

Chemical Property:

• PSA: 92.36000
• Density: 1.312
• LogP: 4.80350
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 354.0917247
• Heavy Atom Count: 23
• Complexity: 489

Purity/Quality:

98%min ^*data from raw suppliers

N-(tert-Butyl)-3-((2-chloro-5-methylpyrimidin-4-yl)amino)benzenesulfonamide 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CN=C(N=C1NC2=CC(=CC=C2)S(=O)(=O)NC(C)(C)C)Cl

Technology Process of N-(tert-Butyl)-3-((2-chloro-5-methylpyrimidin-4-yl)amino)benzenesulfonamide

There total 4 articles about N-(tert-Butyl)-3-((2-chloro-5-methylpyrimidin-4-yl)amino)benzenesulfonamide 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: 98.0%

3-bromo-(N-tert-butyl)benzenesulfonamide (308283-47-8) + 2-chloro-4-amino-5-methylpyrimidine (14394-70-8) → N-(tert-butyl)-3-((2-chloro-5-methylpyrimidin-4-yl)amino)benzenesulfonamide (936092-53-4)

Guidance literature:

With caesium carbonate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; for 3h; Heating / reflux;

Reference yield: 79.0%

2,6-dichloro-5-methylpyrimidine (1780-31-0) + 3-amino-N-(dimethylethyl)benzenesulfonamide (608523-94-0) → N-(tert-butyl)-3-((2-chloro-5-methylpyrimidin-4-yl)amino)benzenesulfonamide (936092-53-4)

Guidance literature:

In methanol; water; at 45 ℃; for 20h; Industry scale; Inert atmosphere;

Reference yield:

3-nitrobenzenesulphonyl chloride (121-51-7) → N-(tert-butyl)-3-((2-chloro-5-methylpyrimidin-4-yl)amino)benzenesulfonamide (936092-53-4)

Guidance literature:

Multi-step reaction with 3 steps

1: tetrahydrofuran / 1 h / 0 - 20 °C / Cooling with ice; Inert atmosphere

2: ammonium chloride; iron / ethanol; water / 85 °C / Inert atmosphere

3: water; methanol / 45 °C / Inert atmosphere

With iron; ammonium chloride; In tetrahydrofuran; methanol; ethanol; water;

upstream raw materials:

3-bromo-(N-tert-butyl)benzenesulfonamide

2-chloro-4-amino-5-methylpyrimidine

2,6-dichloro-5-methylpyrimidine

3-amino-N-(dimethylethyl)benzenesulfonamide

Downstream raw materials:

TG₄₆

Refernces

• 1、 Khorsandi, Zahra,Keshavarzipour, Fariba,Varma, Rajender S.,Hajipour, Abdol R.,Sadeghi-Aliabadi, Hojjat. "Sustainable synthesis of potential antitumor new derivatives of Abemaciclib and Fedratinib via C-N cross coupling reactions using Pd/Cu-free Co-catalyst". . . Retrieved 2021/11/24.
• 2、 Hajipour, Abdol R.,Khorsandi, Zahra,Sarfjoo, Mohamad Reza,Varma, Rajender S.. "A Pd/Cu-Free magnetic cobalt catalyst for C-N cross coupling reactions: synthesis of abemaciclib and fedratinib". supporting information. p. 5222 - 5229. Retrieved 2021/07/29.