2-(4-hydroxy-3,5-dimethylphenyl)-5,7-dimethoxy-3,4-dihydroquinazolin-4-one

Base Information

• Chemical Name: 2-(4-hydroxy-3,5-dimethylphenyl)-5,7-dimethoxy-3,4-dihydroquinazolin-4-one
• CAS No.: 1044870-30-5
• Molecular Formula: C₁₈H₁₈N₂O₄
• Molecular Weight: 326.352
• Mol file: 1044870-30-5.mol

Synonyms:2-(4-hydroxy-3,5-dimethylphenyl)-5,7-dimethoxy-3,4-dihydroquinazolin-4-one

Chemical Property of 2-(4-hydroxy-3,5-dimethylphenyl)-5,7-dimethoxy-3,4-dihydroquinazolin-4-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(4-hydroxy-3,5-dimethylphenyl)-5,7-dimethoxy-3,4-dihydroquinazolin-4-one

There total 11 articles about 2-(4-hydroxy-3,5-dimethylphenyl)-5,7-dimethoxy-3,4-dihydroquinazolin-4-one 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: 79.0%

4-hydroxy-3,5-dimethylbenzaldehyde (2233-18-3) + 2-amino-4,6-dimethoxybenzamide (63920-73-0) → 2-(4-hydroxy-3,5-dimethylphenyl)-5,7-dimethoxy-3,4-dihydroquinazolin-4-one (1044870-30-5)

Guidance literature:

With toluene-4-sulfonic acid; sodium hydrogensulfite; In N,N-dimethyl acetamide; at 120 ℃; for 16h;

DOI:10.1016/j.bmcl.2017.07.054

Reference yield:

2-amino-4,6-dimethoxybenzoic acid (21577-57-1) → 2-(4-hydroxy-3,5-dimethylphenyl)-5,7-dimethoxy-3,4-dihydroquinazolin-4-one (1044870-30-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; 4-methyl-morpholine / tetrahydrofuran / 3 h / 20 °C

1.2: 16 h / 20 °C

2.1: potassium carbonate; iodine / N,N-dimethyl-formamide / 12 h / 80 °C

With 4-methyl-morpholine; iodine; potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; N,N-dimethyl-formamide;

Reference yield:

3.5-dimethoxyaniline (10272-07-8) → 2-(4-hydroxy-3,5-dimethylphenyl)-5,7-dimethoxy-3,4-dihydroquinazolin-4-one (1044870-30-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: hydrogenchloride / diethyl ether / 1.5 h / 0 - 10 °C

2.1: diethyl ether / 2 h / 170 °C

3.1: sodium hydroxide; dihydrogen peroxide / tetrahydrofuran; water / 70 °C

3.2: 3 h / 20 °C

3.3: 16 h / 20 °C

4.1: potassium carbonate; iodine / N,N-dimethyl-formamide / 12 h / 80 °C

With hydrogenchloride; dihydrogen peroxide; iodine; potassium carbonate; sodium hydroxide; In tetrahydrofuran; diethyl ether; water; N,N-dimethyl-formamide;

upstream raw materials:

4-hydroxy-3,5-dimethylbenzaldehyde

2-amino-4,6-dimethoxybenzamide

4,6-dimethoxyindoline-2,3-dione

3,5-dimethoxyaniline hydrochloride

Downstream raw materials:

2-(4-(2-hydroxyethoxy)-3,5-dimethylphenyl)-5,7-dimethoxy-3,4-dihydroquinazoline-4-one

Refernces

• 1、 Yu, Ping,Liu, Wenjing,Ren, Jinghui,Wang, Yingying,Ning, Yao,Huang, Mingqi,Hu,Wei, Lili,Ji, Min,Cai, Jin. "Design, synthesis and biological evaluation of hypolipidemic compounds based on BRD4 inhibitor RVX-208". supporting information. p. 2168 - 2172. Retrieved 2019/07/03.
• 2、 Shao, Mingfeng,He, Linhong,Zheng, Li,Huang, Lingxiao,Zhou, Yuanyuan,Wang, Taijing,Chen, Yong,Shen, Mingsheng,Wang, Fang,Yang, Zhuang,Chen, Lijuan. "Structure-based design, synthesis and in vitro antiproliferative effects studies of novel dual BRD4/HDAC inhibitors". supporting information. p. 4051 - 4055. Retrieved 2017/08/22.