2-((E)-2-(5-Bromo-3-methyl-2-methylthioimidazol-4-yl)ethenyl)-5-methylpyrazine

Base Information

• Chemical Name: 2-((E)-2-(5-Bromo-3-methyl-2-methylthioimidazol-4-yl)ethenyl)-5-methylpyrazine
• CAS No.: 108905-66-4
• Molecular Formula: C₁₂H₁₃BrN₄S
• Molecular Weight: 325.232
• Mol file: 108905-66-4.mol

Synonyms:2-((E)-2-(5-Bromo-3-methyl-2-methylthioimidazol-4-yl)ethenyl)-5-methylpyrazine;Pyrazine, 2-(2-(4-bromo-1-methyl-2-(methylthio)-1H-imidazol-5-yl)ethenyl)-5-methyl-, (E)-;108905-66-4;C12-H13-Br-N4-S

Chemical Property of 2-((E)-2-(5-Bromo-3-methyl-2-methylthioimidazol-4-yl)ethenyl)-5-methylpyrazine

Chemical Property:

• Vapor Pressure: 5.47E-09mmHg at 25°C
• Boiling Point: 469.5°Cat760mmHg
• Flash Point: 237.8°C
• Density: 1.49g/cm³
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 324.00443
• Heavy Atom Count: 18
• Complexity: 302

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CN=C(C=N1)C=CC2=C(N=C(N2C)SC)Br
• Isomeric SMILES: CC1=CN=C(C=N1)/C=C/C2=C(N=C(N2C)SC)Br

Technology Process of 2-((E)-2-(5-Bromo-3-methyl-2-methylthioimidazol-4-yl)ethenyl)-5-methylpyrazine

There total 4 articles about 2-((E)-2-(5-Bromo-3-methyl-2-methylthioimidazol-4-yl)ethenyl)-5-methylpyrazine 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: 84.5%

2-(5-methyl-2-pyrazinyl)-1-(4-bromo-1-methyl-2-(methylthio)-5-imidazolyl)ethan-1-ol (108905-65-3) → 2-(5-methyl-2-pyrazinyl)-1-(4-bromo-1-methyl-2-(methylthio)-5-imidazolyl)ethene (108905-66-4)

Guidance literature:

With methanesulfonic acid; In toluene; for 0.333333h; Heating;

DOI:10.1021/jo00031a017

Reference yield:

2,5-dimethyl-pyrazine (123-32-0) → 2-(5-methyl-2-pyrazinyl)-1-(4-bromo-1-methyl-2-(methylthio)-5-imidazolyl)ethene (108905-66-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 1) LDA / 1) THF, hexanes, -78 deg C, 2) -19 to -15 deg C

2: 79 percent / NaBH₄ / tetrahydrofuran; propan-2-ol / a) 0 deg C to room temperature, overnight, b) 0 deg C to room temperature, 8 h

3: 84.5 percent / methanesulfonic acid / toluene / 0.33 h / Heating

With sodium tetrahydroborate; methanesulfonic acid; lithium diisopropyl amide; In tetrahydrofuran; isopropyl alcohol; toluene;

DOI:10.1021/jo00031a017

Reference yield:

Methyl 4-bromo-1-methyl-2-methylthio-5-imidazolecarboxylate (108905-63-1) → 2-(5-methyl-2-pyrazinyl)-1-(4-bromo-1-methyl-2-(methylthio)-5-imidazolyl)ethene (108905-66-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 1) LDA / 1) THF, hexanes, -78 deg C, 2) -19 to -15 deg C

2: 79 percent / NaBH₄ / tetrahydrofuran; propan-2-ol / a) 0 deg C to room temperature, overnight, b) 0 deg C to room temperature, 8 h

3: 84.5 percent / methanesulfonic acid / toluene / 0.33 h / Heating

With sodium tetrahydroborate; methanesulfonic acid; lithium diisopropyl amide; In tetrahydrofuran; isopropyl alcohol; toluene;

DOI:10.1021/jo00031a017

upstream raw materials:

2-(5-methyl-2-pyrazinyl)-1-(4-bromo-1-methyl-2-(methylthio)-5-imidazolyl)ethan-1-ol

2,5-dimethyl-pyrazine

Methyl 4-bromo-1-methyl-2-methylthio-5-imidazolecarboxylate

2-(5-methyl-2-pyrazinyl)-1-(4-bromo-1-methyl-2-(methylthio)-5-imidazolyl)ethan-1-one

Downstream raw materials:

3,8-dimethyl-2-(methylthio)-imidazo<4,5-f>quinoxaline