(E)-N-(4-(4-amino-3-(4-chlorophenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)phenyl)-4-(dimethylamino)-N-methylbut-2-enamide

Base Information

• Chemical Name: (E)-N-(4-(4-amino-3-(4-chlorophenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)phenyl)-4-(dimethylamino)-N-methylbut-2-enamide
• CAS No.: 1422827-13-1
• Molecular Formula: C₂₄H₂₄ClN₇O
• Molecular Weight: 461.954
• Mol file: 1422827-13-1.mol

Synonyms:(E)-N-(4-(4-amino-3-(4-chlorophenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)phenyl)-4-(dimethylamino)-N-methylbut-2-enamide

Chemical Property of (E)-N-(4-(4-amino-3-(4-chlorophenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)phenyl)-4-(dimethylamino)-N-methylbut-2-enamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-N-(4-(4-amino-3-(4-chlorophenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)phenyl)-4-(dimethylamino)-N-methylbut-2-enamide

There total 10 articles about (E)-N-(4-(4-amino-3-(4-chlorophenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)phenyl)-4-(dimethylamino)-N-methylbut-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: 25.0%

(E)-N-(4-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)phenyl)-4-(dimethylamino)-N-methylbut-2-enamide (1422828-06-5) + 4-Chlorophenylboronic acid (1679-18-1) → (E)-N-(4-(4-amino-3-(4-chlorophenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)phenyl)-4-(dimethylamino)-N-methylbut-2-enamide (1422827-13-1)

Guidance literature:

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium phosphate tribasic trihydrate; In 1,2-dimethoxyethane; water; at 80 ℃; Inert atmosphere;

Reference yield:

4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidine (151266-23-8) → (E)-N-(4-(4-amino-3-(4-chlorophenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)phenyl)-4-(dimethylamino)-N-methylbut-2-enamide (1422827-13-1)

Guidance literature:

Multi-step reaction with 7 steps

1.1: potassium carbonate / N,N-dimethyl-formamide / 24 h / 100 °C / Inert atmosphere

2.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -40 °C / Inert atmosphere

2.2: -40 - 20 °C

3.1: water; iron; ammonium chloride / tetrahydrofuran; ethanol / 2 h / 50 °C / Inert atmosphere

4.1: tetrahydrofuran; water / 4 h / 30 °C / Inert atmosphere

4.2: 1 h / 30 °C

4.3: 30 °C

5.1: dichloromethane / 20 °C

6.1: trifluoroacetic acid / dichloromethane / 3 h

7.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium phosphate tribasic trihydrate / 1,2-dimethoxyethane; water / 80 °C / Inert atmosphere

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium phosphate tribasic trihydrate; water; iron; potassium carbonate; ammonium chloride; trifluoroacetic acid; lithium hexamethyldisilazane; In tetrahydrofuran; 1,2-dimethoxyethane; ethanol; dichloromethane; water; N,N-dimethyl-formamide; 7.1: |Suzuki Coupling;

Reference yield:

4-Fluoronitrobenzene (350-46-9,178603-76-4) → (E)-N-(4-(4-amino-3-(4-chlorophenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)phenyl)-4-(dimethylamino)-N-methylbut-2-enamide (1422827-13-1)

Guidance literature:

Multi-step reaction with 7 steps

1.1: potassium carbonate / N,N-dimethyl-formamide / 24 h / 100 °C / Inert atmosphere

2.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -40 °C / Inert atmosphere

2.2: -40 - 20 °C

3.1: water; iron; ammonium chloride / tetrahydrofuran; ethanol / 2 h / 50 °C / Inert atmosphere

4.1: tetrahydrofuran; water / 4 h / 30 °C / Inert atmosphere

4.2: 1 h / 30 °C

4.3: 30 °C

5.1: dichloromethane / 20 °C

6.1: trifluoroacetic acid / dichloromethane / 3 h

7.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium phosphate tribasic trihydrate / 1,2-dimethoxyethane; water / 80 °C / Inert atmosphere

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium phosphate tribasic trihydrate; water; iron; potassium carbonate; ammonium chloride; trifluoroacetic acid; lithium hexamethyldisilazane; In tetrahydrofuran; 1,2-dimethoxyethane; ethanol; dichloromethane; water; N,N-dimethyl-formamide; 7.1: |Suzuki Coupling;

upstream raw materials:

(E)-N-(4-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)phenyl)-4-(dimethylamino)-N-methylbut-2-enamide

4-Chlorophenylboronic acid

4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidine

4-Fluoronitrobenzene