2-(1-(4-amino-3-(3-hydroxyprop-1-ynyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-5-fluoro-3-(3-fluorophenyl)-4H-chromen-4-one

Base Information

• Chemical Name: 2-(1-(4-amino-3-(3-hydroxyprop-1-ynyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-5-fluoro-3-(3-fluorophenyl)-4H-chromen-4-one
• CAS No.: 1408086-28-1
• Molecular Formula: C₂₅H₁₇F₂N₅O₃
• Molecular Weight: 473.438
• Mol file: 1408086-28-1.mol

Synonyms:2-(1-(4-amino-3-(3-hydroxyprop-1-ynyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-5-fluoro-3-(3-fluorophenyl)-4H-chromen-4-one

Chemical Property of 2-(1-(4-amino-3-(3-hydroxyprop-1-ynyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-5-fluoro-3-(3-fluorophenyl)-4H-chromen-4-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(1-(4-amino-3-(3-hydroxyprop-1-ynyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-5-fluoro-3-(3-fluorophenyl)-4H-chromen-4-one

There total 11 articles about 2-(1-(4-amino-3-(3-hydroxyprop-1-ynyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-5-fluoro-3-(3-fluorophenyl)-4H-chromen-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: 29.0%

2-(1-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-5-fluoro-3-(3-fluorophenyl)-4H-chromen-4-one (1408087-88-6) + propargyl alcohol (107-19-7) → 2-(1-(4-amino-3-(3-hydroxyprop-1-ynyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-5-fluoro-3-(3-fluorophenyl)-4H-chromen-4-one (1408086-28-1)

Guidance literature:

With 2-(1-(4-amino-3-(4-methoxy-3,5-dimethylphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-5-fluoro-3-(3-fluorophenyl)-4H-chromen-4-one; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; for 4h; Inert atmosphere; Reflux;

Reference yield:

1-(2-Fluoro-6-methoxyphenyl)ethanone (120484-50-6) → 2-(1-(4-amino-3-(3-hydroxyprop-1-ynyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-5-fluoro-3-(3-fluorophenyl)-4H-chromen-4-one (1408086-28-1)

Guidance literature:

Multi-step reaction with 8 steps

1.1: aluminum (III) chloride / dichloromethane / 12 h / 20 °C

2.1: dichloromethane / 3 h / 45 °C / Cooling with ice

3.1: sodium hydride / dimethyl sulfoxide / 13 h / 0 - 20 °C

3.2: 12 h / Reflux

4.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 12 h / 20 °C

5.1: potassium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane; water / 12 h / Reflux; Inert atmosphere

6.1: N-Bromosuccinimide / 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 12 h / 80 °C

7.1: potassium carbonate / N,N-dimethyl-formamide / 12 h / 20 °C

8.1: 2-(1-(4-amino-3-(4-methoxy-3,5-dimethylphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-5-fluoro-3-(3-fluorophenyl)-4H-chromen-4-one / tetrakis(triphenylphosphine) palladium⁽⁰⁾; copper(l) iodide / tetrahydrofuran / 4 h / Inert atmosphere; Reflux

With aluminum (III) chloride; N-Bromosuccinimide; 2-(1-(4-amino-3-(4-methoxy-3,5-dimethylphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-5-fluoro-3-(3-fluorophenyl)-4H-chromen-4-one; sodium hydride; potassium carbonate; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 2,2'-azobis(isobutyronitrile); In tetrahydrofuran; 1,4-dioxane; tetrachloromethane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide;

Reference yield:

1-(2-fluoro-6-hydroxyphenyl)ethan-1-one (93339-98-1) → 2-(1-(4-amino-3-(3-hydroxyprop-1-ynyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-5-fluoro-3-(3-fluorophenyl)-4H-chromen-4-one (1408086-28-1)

Guidance literature:

Multi-step reaction with 7 steps

1.1: dichloromethane / 3 h / 45 °C / Cooling with ice

2.1: sodium hydride / dimethyl sulfoxide / 13 h / 0 - 20 °C

2.2: 12 h / Reflux

3.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 12 h / 20 °C

4.1: potassium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane; water / 12 h / Reflux; Inert atmosphere

5.1: N-Bromosuccinimide / 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 12 h / 80 °C

6.1: potassium carbonate / N,N-dimethyl-formamide / 12 h / 20 °C

7.1: 2-(1-(4-amino-3-(4-methoxy-3,5-dimethylphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-5-fluoro-3-(3-fluorophenyl)-4H-chromen-4-one / tetrakis(triphenylphosphine) palladium⁽⁰⁾; copper(l) iodide / tetrahydrofuran / 4 h / Inert atmosphere; Reflux

With N-Bromosuccinimide; 2-(1-(4-amino-3-(4-methoxy-3,5-dimethylphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-5-fluoro-3-(3-fluorophenyl)-4H-chromen-4-one; sodium hydride; potassium carbonate; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 2,2'-azobis(isobutyronitrile); In tetrahydrofuran; 1,4-dioxane; tetrachloromethane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide;

upstream raw materials:

1-(2-Fluoro-6-methoxyphenyl)ethanone

1-(2-fluoro-6-hydroxyphenyl)ethan-1-one

2-(1-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-5-fluoro-3-(3-fluorophenyl)-4H-chromen-4-one

propargyl alcohol