2,4-Dimethoxy-5-(4-methoxyphenyl)pyrrolo<2,3-d>pyrimidine-6-yl 4-methoxyphenyl ketone

Base Information

• Chemical Name: 2,4-Dimethoxy-5-(4-methoxyphenyl)pyrrolo<2,3-d>pyrimidine-6-yl 4-methoxyphenyl ketone
• CAS No.: 175791-66-9
• Molecular Formula: C₂₃H₂₁N₃O₅
• Molecular Weight: 419.437
• Mol file: 175791-66-9.mol

Synonyms:2,4-Dimethoxy-5-(4-methoxyphenyl)pyrrolo<2,3-d>pyrimidine-6-yl 4-methoxyphenyl ketone

Chemical Property of 2,4-Dimethoxy-5-(4-methoxyphenyl)pyrrolo<2,3-d>pyrimidine-6-yl 4-methoxyphenyl ketone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,4-Dimethoxy-5-(4-methoxyphenyl)pyrrolo<2,3-d>pyrimidine-6-yl 4-methoxyphenyl ketone

There total 14 articles about 2,4-Dimethoxy-5-(4-methoxyphenyl)pyrrolo<2,3-d>pyrimidine-6-yl 4-methoxyphenyl ketone 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: 60.0%

4-methoxylphenylboronic acid 1,3-propanediol ester (155826-85-0) + 5-Iodo-2,4-dimethoxypyrrolo<2,3-d>pyrimidin-6-yl 4-methoxyphenyl ketone (175791-65-8) → 2,4-Dimethoxy-5-(4-methoxyphenyl)pyrrolo<2,3-d>pyrimidine-6-yl 4-methoxyphenyl ketone (175791-66-9)

Guidance literature:

tetrakis(triphenylphosphine) palladium⁽⁰⁾; In N,N-dimethyl-formamide; at 100 ℃;

DOI:10.1016/S0040-4039(00)76660-3

Reference yield: 57.0%

4-methoxyphenylboronic acid (5720-07-0) + 5-Iodo-2,4-dimethoxypyrrolo<2,3-d>pyrimidin-6-yl 4-methoxyphenyl ketone (175791-65-8) → 2,4-Dimethoxy-5-(4-methoxyphenyl)pyrrolo<2,3-d>pyrimidine-6-yl 4-methoxyphenyl ketone (175791-66-9)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; In 1,4-dioxane; water; at 70 ℃; for 24h; Inert atmosphere;

DOI:10.1002/chem.201602519

Reference yield:

2,4-dimethoxy-7H-pyrrolo<2,3-d>pyrimidine (90057-09-3) → 2,4-Dimethoxy-5-(4-methoxyphenyl)pyrrolo<2,3-d>pyrimidine-6-yl 4-methoxyphenyl ketone (175791-66-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 95 percent / NaH / tetrahydrofuran / 1.) r.t., 1 h, 2.) r.t., 1 h

2: 55 percent / t-BuLi / tetrahydrofuran; pentane / 1.) -78 deg C, 0.5 h, 2.) -78 deg C, 2 h

3: 91 percent / KOH / tetrahydrofuran; methanol / 2 h / Ambient temperature

4: 86 percent / I₂, KOH / dimethylformamide / 2 h / Ambient temperature

5: 1.) propane-1,3-diol, MgSO₄, 2.) K₃PO₄ / 2.) 3)4> / 1.) C₆H₆, r.t., 24 h, 2.) DMF, 6 h

With potassium hydroxide; potassium phosphate; iodine; tert.-butyl lithium; sodium hydride; magnesium sulfate; trimethyleneglycol; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; pentane;

DOI:10.1039/p19960000459

upstream raw materials:

4-methoxylphenylboronic acid 1,3-propanediol ester

5-Iodo-2,4-dimethoxypyrrolo<2,3-d>pyrimidin-6-yl 4-methoxyphenyl ketone

4-methoxyphenylboronic acid

4,N-dimethoxy-N-methylbenzamide

Downstream raw materials:

6-(4-hydroxybenzoyl)-5-(4-hydroxyphenyl)-1H-pyrrolo[2,3-d]pyrimidine-2,4(3H,7H)-dione

Refernces

• 1、 Sakamoto, Takao,Kondo, Yoshinori,Sato, Shuichiroh,Yamanaka, Hiroshi. "Condensed heteroaromatic ring systems. Part 24. Synthesis of rigidin, a pyrrolo[2,3-d]pynmidine marine alkaloid". . p. 459 - 464. Retrieved 2007/10/03.