N-(3-((6-((1-methyl-1H-pyrazol-4-yl)amino)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)phenyl)acrylamide

Base Information

• Chemical Name: N-(3-((6-((1-methyl-1H-pyrazol-4-yl)amino)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)phenyl)acrylamide
• CAS No.: 1428444-17-0
• Molecular Formula: C₁₉H₁₈N₈O
• Molecular Weight: 374.405
• Mol file: 1428444-17-0.mol

Synonyms:N-(3-((6-((1-methyl-1H-pyrazol-4-yl)amino)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)phenyl)acrylamide

Chemical Property of N-(3-((6-((1-methyl-1H-pyrazol-4-yl)amino)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)phenyl)acrylamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(3-((6-((1-methyl-1H-pyrazol-4-yl)amino)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)phenyl)acrylamide

There total 9 articles about N-(3-((6-((1-methyl-1H-pyrazol-4-yl)amino)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)phenyl)acrylamide 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: 82.0%

1-(3-aminobenzyl)-N-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine (1428444-29-4) + acryloyl chloride (814-68-6,25189-84-8) → N-(3-((6-((1-methyl-1H-pyrazol-4-yl)amino)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)phenyl)acrylamide (1428444-17-0)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at -5 ℃; for 0.5h;

DOI:10.1016/j.bioorg.2020.103720

Reference yield:

6-chloro-1H-pyrazolo[3,4-d]pyrimidine (23002-51-9) → N-(3-((6-((1-methyl-1H-pyrazol-4-yl)amino)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)phenyl)acrylamide (1428444-17-0)

Guidance literature:

Multi-step reaction with 4 steps

1: potassium carbonate / acetonitrile / 20 h / 20 °C

2: hydrogenchloride / isopropyl alcohol; water / 18 h / 90 °C

3: hydrogenchloride; palladium on activated charcoal; hydrogen / water; methanol / 2 h

4: N-ethyl-N,N-diisopropylamine / dichloromethane; N,N-dimethyl-formamide / 16 h / 20 °C

With hydrogenchloride; palladium on activated charcoal; hydrogen; potassium carbonate; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane; water; N,N-dimethyl-formamide; isopropyl alcohol; acetonitrile;

Reference yield:

N-(1-methyl-1H-pyrazol-4-yl)-1-(3-nitrobenzyl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine (1428444-28-3) → N-(3-((6-((1-methyl-1H-pyrazol-4-yl)amino)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)phenyl)acrylamide (1428444-17-0)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogenchloride; palladium on activated charcoal; hydrogen / water; methanol / 2 h

2: N-ethyl-N,N-diisopropylamine / dichloromethane; N,N-dimethyl-formamide / 16 h / 20 °C

With hydrogenchloride; palladium on activated charcoal; hydrogen; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane; water; N,N-dimethyl-formamide;

upstream raw materials:

6-chloro-1H-pyrazolo[3,4-d]pyrimidine

1-bromomethyl-3-nitrobenzene

6-chloro-1-(3-nitrobenzyl)-1H-pyrazolo[3,4-d]pyrimidine

N-(1-methyl-1H-pyrazol-4-yl)-1-(3-nitrobenzyl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine