(E)-8-(4-Bromostyryl)-1,3-diethyl-7-methylxanthine

Base Information

• Chemical Name: (E)-8-(4-Bromostyryl)-1,3-diethyl-7-methylxanthine
• CAS No.: 155271-71-9
• Molecular Formula: C₁₈H₁₉BrN₄O₂
• Molecular Weight: 403.278
• Wikidata: Q76389458
• Mol file: 155271-71-9.mol

Synonyms:(E)-8-(4-Bromostyryl)-1,3-diethyl-7-methylxanthine;155271-71-9;(E)-8-(2-(4-Bromophenyl)ethenyl)-1,3-diethyl-7-methyl-3,7-dihydro-1H-purine-2,6-dione;1H-Purine-2,6-dione, 3,7-dihydro-8-(2-(4-bromophenyl)ethenyl)-1,3-diethyl-7-methyl-, (E)-;SCHEMBL7312446;SCHEMBL7312458;BDBM110149;LS-126606;(E)-8-(4-Bromostyryl)-1,3-diethyl-7-methylxanthine (6e)

Chemical Property of (E)-8-(4-Bromostyryl)-1,3-diethyl-7-methylxanthine

Chemical Property:

• Vapor Pressure: 1.09E-13mmHg at 25°C
• Boiling Point: 585.4°Cat760mmHg
• Flash Point: 307.9°C
• Density: 1.44g/cm³
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 402.06914
• Heavy Atom Count: 25
• Complexity: 547

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCN1C2=C(C(=O)N(C1=O)CC)N(C(=N2)C=CC3=CC=C(C=C3)Br)C
• Isomeric SMILES: CCN1C2=C(C(=O)N(C1=O)CC)N(C(=N2)/C=C/C3=CC=C(C=C3)Br)C

Technology Process of (E)-8-(4-Bromostyryl)-1,3-diethyl-7-methylxanthine

There total 3 articles about (E)-8-(4-Bromostyryl)-1,3-diethyl-7-methylxanthine 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: 90.7%

→ (E)-8-(4-bromostyryl)-1,3-diethyl-7-methyl-1H-purine-2,6(3H,7H)-dione (155271-71-9)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 0.166667h;

In N,N-dimethyl-formamide; at 25 ℃; for 3h;

Reference yield: 26.0%

(E)-8-(4-bromostyryl)-1,3-diethyl-1H-purine-2,6(3H,7H)-dione (155271-70-8) + methyl iodide (74-88-4) → (E)-8-(4-bromostyryl)-1,3-diethyl-7-methyl-1H-purine-2,6(3H,7H)-dione (155271-71-9)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 90 ℃; for 2h;

DOI:10.1016/j.bioorg.2013.06.006

Reference yield:

5,6-diamino-1,3-diethyluracil (52998-22-8) + trans-4-bromocinnamic acid (1200-07-3,5676-63-1,17916-60-8) → (E)-8-(4-bromostyryl)-1,3-diethyl-7-methyl-1H-purine-2,6(3H,7H)-dione (155271-71-9)

Guidance literature:

Multi-step reaction with 2 steps

1: N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; hydrogenchloride / 1,4-dioxane; water / 2 h / 20 °C / pH 5

2: potassium carbonate / N,N-dimethyl-formamide / 2 h / 90 °C

With hydrogenchloride; potassium carbonate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In 1,4-dioxane; water; N,N-dimethyl-formamide;

DOI:10.1016/j.bioorg.2013.06.006

upstream raw materials:

(E)-8-(4-bromostyryl)-1,3-diethyl-1H-purine-2,6(3H,7H)-dione

methyl iodide

5,6-diamino-1,3-diethyluracil

trans-4-bromocinnamic acid