4-{3-[1-(4-amino-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl}-N,N-dimethylpyridine-2-carboxamide

Base Information

• Chemical Name: 4-{3-[1-(4-amino-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl}-N,N-dimethylpyridine-2-carboxamide
• CAS No.: 1426695-57-9
• Molecular Formula: C₂₃H₂₄ClN₇O₂
• Molecular Weight: 465.942
• Mol file: 1426695-57-9.mol

Synonyms:

Chemical Property of 4-{3-[1-(4-amino-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl}-N,N-dimethylpyridine-2-carboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-{3-[1-(4-amino-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl}-N,N-dimethylpyridine-2-carboxamide

There total 7 articles about 4-{3-[1-(4-amino-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl}-N,N-dimethylpyridine-2-carboxamide 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:

4-aminopyrazolo[3,4-d]pyrimidine (64834-00-0) + 4-[3-chloro-5-(1-chloroethyl)-6-methoxy-2-methylphenyl]pyridine-2-carbonitrile (1426699-20-8) + dimethyl amine (124-40-3) → 4-{3-[1-(4-amino-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl}-N,N-dimethylpyridine-2-carboxamide (1426695-57-9)

Guidance literature:

4-aminopyrazolo[3,4-d]pyrimidine; 4-[3-chloro-5-(1-chloroethyl)-6-methoxy-2-methylphenyl]pyridine-2-carbonitrile; With sodium hydride; In N,N-dimethyl-formamide; at 30 ℃; Inert atmosphere;

With water; sodium hydroxide; In ethanol; at 95 ℃; for 6h; Inert atmosphere;

dimethyl amine; With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; In tetrahydrofuran; N,N-dimethyl-formamide; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1021/acsmedchemlett.9b00334

Reference yield:

1-(3-bromo-5-chloro-2-methoxy-4-methylphenyl)ethanol (1382996-38-4) → 4-{3-[1-(4-amino-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl}-N,N-dimethylpyridine-2-carboxamide (1426695-57-9)

Guidance literature:

Multi-step reaction with 5 steps

1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium carbonate / acetonitrile; water / 2 h / 95 °C / Inert atmosphere

2: 1,3,5-trichloro-2,4,6-triazine; N,N-dimethyl-formamide / dichloromethane / 20 °C

3: sodium hydride / N,N-dimethyl-formamide / 30 °C

4: water; sodium hydroxide / ethanol / 6 h / 95 °C

5: triethylamine; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / N,N-dimethyl-formamide; tetrahydrofuran / 1 h / 20 °C

With 1,3,5-trichloro-2,4,6-triazine; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; water; sodium hydride; sodium carbonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; N,N-dimethyl-formamide; sodium hydroxide; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

Reference yield:

4-[3-chloro-5-(1-hydroxyethyl)-6-methoxy-2-methylphenyl]pyridine-2-carbonitrile (1426699-19-5) → 4-{3-[1-(4-amino-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl}-N,N-dimethylpyridine-2-carboxamide (1426695-57-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 1,3,5-trichloro-2,4,6-triazine; N,N-dimethyl-formamide / dichloromethane / 20 °C

2: sodium hydride / N,N-dimethyl-formamide / 30 °C

3: water; sodium hydroxide / ethanol / 6 h / 95 °C

4: triethylamine; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / N,N-dimethyl-formamide; tetrahydrofuran / 1 h / 20 °C

With 1,3,5-trichloro-2,4,6-triazine; water; sodium hydride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; N,N-dimethyl-formamide; sodium hydroxide; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide;

upstream raw materials:

4-{3-[1-(4-amino-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl}pyridine-2-carbonitrile

1-(3-bromo-5-chloro-2-methoxy-4-methylphenyl)ethanone

1-(5-chloro-2-methoxy-4-methylphenyl)ethanone

1-(3-bromo-5-chloro-2-methoxy-4-methylphenyl)ethanol