3-(3-(3-hydroxyphenyl)prop-2-yn-1-yl)-1,7-dimethyl-8-(methylsulfonyl)-3,7-dihydro-1H-purine-2,6-dione

Base Information

• Chemical Name: 3-(3-(3-hydroxyphenyl)prop-2-yn-1-yl)-1,7-dimethyl-8-(methylsulfonyl)-3,7-dihydro-1H-purine-2,6-dione
• CAS No.: 2093393-05-4
• Molecular Formula: C₁₇H₁₆N₄O₅S
• Molecular Weight: 388.404
• Mol file: 2093393-05-4.mol

Synonyms:

Chemical Property of 3-(3-(3-hydroxyphenyl)prop-2-yn-1-yl)-1,7-dimethyl-8-(methylsulfonyl)-3,7-dihydro-1H-purine-2,6-dione

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

3,7-Dihydro-3-[3-(3-hydroxyphenyl)-2-propyn-1-yl]-1,7-dimethyl-8-(methylsulfonyl)-1H-purine-2,6-dione ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: 3,7-Dihydro-3-[3-(3-hydroxyphenyl)-2-propyn-1-yl]-1,7-dimethyl-8-(methylsulfonyl)-1H-purine-2,6-dione, also known as TC13172, is a highly potent Mixed Lineage Kinase Domain-Like protein (MLKL) inhibitor.

Technology Process of 3-(3-(3-hydroxyphenyl)prop-2-yn-1-yl)-1,7-dimethyl-8-(methylsulfonyl)-3,7-dihydro-1H-purine-2,6-dione

There total 10 articles about 3-(3-(3-hydroxyphenyl)prop-2-yn-1-yl)-1,7-dimethyl-8-(methylsulfonyl)-3,7-dihydro-1H-purine-2,6-dione 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: 87.0%

1,7-dimethyl-8-(methylsulfonyl)-1H-purine-2,6(3H,7H)-dione + 3-(3-bromoprop-1-yn-1-yl)phenol → 3-(3-(3-hydroxyphenyl)prop-2-yn-1-yl)-1,7-dimethyl-8-(methylsulfonyl)-3,7-dihydro-1H-purine-2,6-dione (2093393-05-4)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 0.5h; Inert atmosphere;

Reference yield:

3-(3-(3-hydroxyphenyl)prop-2-yn-1-yl)-1,7-dimethyl-8-(methylthio)-3,7-dihydro-1H-purine-2,6-dione → 3-(3-(3-hydroxyphenyl)prop-2-yn-1-yl)-1,7-dimethyl-8-(methylsulfonyl)-3,7-dihydro-1H-purine-2,6-dione (2093393-05-4)

Guidance literature:

With Oxone; In water; at 20 ℃;

DOI:10.1039/c7cc00667e

Reference yield:

8-chloro-1,7-dimethyl-1H-purine-2,6(3H,7H)-dione (5472-54-8) → 3-(3-(3-hydroxyphenyl)prop-2-yn-1-yl)-1,7-dimethyl-8-(methylsulfonyl)-3,7-dihydro-1H-purine-2,6-dione (2093393-05-4)

Guidance literature:

Multi-step reaction with 4 steps

1: N,N-dimethyl-formamide; water / Microwave irradiation

2: potassium carbonate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

3: copper(l) iodide; triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 60 °C / Inert atmosphere

4: Oxone / water / 20 °C

With Oxone; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; triethylamine; In water; N,N-dimethyl-formamide; 3: |Sonogashira Cross-Coupling;

DOI:10.1039/c7cc00667e

upstream raw materials:

paraxanthine

8-chloro-1,7-dimethyl-1H-purine-2,6(3H,7H)-dione

4-amino-1-methylimidazole-5-carboxylate ethyl ester

3-Iodophenol

Refernces

• 1、 Yan, Bo,Liu, Lei,Huang, Shaoqiang,Ren, Yan,Wang, Huayi,Yao, Zhenglin,Li, Lin,Chen, She,Wang, Xiaodong,Zhang, Zhiyuan. "Discovery of a new class of highly potent necroptosis inhibitors targeting the mixed lineage kinase domain-like protein". . p. 3637 - 3640. Retrieved 2017/04/03.