(E)-N-(4-((3-bromo-4-chlorophenyl)amino)pyrido[3,4-d]pyrimidin-6-yl)-4-(dimethylamino)but-2-enamide

Base Information

• Chemical Name: (E)-N-(4-((3-bromo-4-chlorophenyl)amino)pyrido[3,4-d]pyrimidin-6-yl)-4-(dimethylamino)but-2-enamide
• CAS No.: 2135696-72-7
• Molecular Formula: C₁₉H₁₈BrClN₆O
• Molecular Weight: 461.749
• Mol file: 2135696-72-7.mol

Synonyms:

Chemical Property of (E)-N-(4-((3-bromo-4-chlorophenyl)amino)pyrido[3,4-d]pyrimidin-6-yl)-4-(dimethylamino)but-2-enamide

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-N-(4-((3-bromo-4-chlorophenyl)amino)pyrido[3,4-d]pyrimidin-6-yl)-4-(dimethylamino)but-2-enamide

There total 10 articles about (E)-N-(4-((3-bromo-4-chlorophenyl)amino)pyrido[3,4-d]pyrimidin-6-yl)-4-(dimethylamino)but-2-enamide 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: 60.9%

2-(N,N-dimethylamino)ethoxide (52334-92-6) + diethyl (2-((4-((3-bromo-4-chlorophenyl)amino)pyrido[3,4-d]pyrimidin-6-yl)amino)-2-oxoethyl)phosphonate → (E)-N-(4-((3-bromo-4-chlorophenyl)amino)pyrido[3,4-d]pyrimidin-6-yl)-4-(dimethylamino)but-2-enamide (2135696-72-7)

Guidance literature:

With lithium chloride; potassium hydroxide; In tetrahydrofuran; N,N-dimethyl acetamide; water; at 0 ℃; for 2.95h;

Reference yield: 60.9%

1,1-dimethoxymethyl-N,N-dimethylmethanamine (38711-20-5) + diethyl (2-((4-((3-bromo-4-chlorophenyl)amino)pyrido[3,4-d]pyrimidin-6-yl)amino)-2-oxoethyl)phosphonate → (E)-N-(4-((3-bromo-4-chlorophenyl)amino)pyrido[3,4-d]pyrimidin-6-yl)-4-(dimethylamino)but-2-enamide (2135696-72-7)

Guidance literature:

1,1-dimethoxymethyl-N,N-dimethylmethanamine; With hydrogenchloride; In water; at 40 ℃; for 20h;

diethyl (2-((4-((3-bromo-4-chlorophenyl)amino)pyrido[3,4-d]pyrimidin-6-yl)amino)-2-oxoethyl)phosphonate; With lithium chloride; potassium hydroxide; In tetrahydrofuran; N,N-dimethyl acetamide; water; at 0 ℃; for 2.25h; Inert atmosphere;

Reference yield:

6-fluoro-4-oxo-3H-pyrido[3,4-d]pyrimidine (171178-44-2) → (E)-N-(4-((3-bromo-4-chlorophenyl)amino)pyrido[3,4-d]pyrimidin-6-yl)-4-(dimethylamino)but-2-enamide (2135696-72-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: thionyl chloride; N,N-dimethyl-formamide / 2 h / Reflux

2.1: N,N-dimethyl acetamide / 16 h / 30 °C

3.1: dimethyl sulfoxide / 16 h / 100 °C

4.1: trifluoroacetic acid / dichloromethane / 16 h / 20 °C

4.2: 0.08 h

5.1: 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine / ethyl acetate / 16 h / 30 °C

6.1: potassium hydroxide; lithium chloride / water; N,N-dimethyl acetamide; tetrahydrofuran / 2.95 h / 0 °C

With thionyl chloride; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; N,N-dimethyl-formamide; trifluoroacetic acid; lithium chloride; potassium hydroxide; In tetrahydrofuran; dichloromethane; N,N-dimethyl acetamide; water; dimethyl sulfoxide; ethyl acetate;

upstream raw materials:

5-Amino-2-fluoropyridine-4-carboxylic acid

6-fluoro-4-oxo-3H-pyrido[3,4-d]pyrimidine

4-chloro-6-fluoro-pyrido[3,4-d]pyrimidine

(6-fluoro-pyridin-3-yl)-carbamic acid, tert-butyl ester

Refernces

• 1、 -. "HETEROCYCLIC INHIBITORS OF TYROSINE KINASE". . . Retrieved 2020/11/03.