N-(5-(5-chloro-2-methoxyphenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide

Base Information

• Chemical Name: N-(5-(5-chloro-2-methoxyphenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide
• CAS No.: 1260168-98-6
• Molecular Formula: C₂₃H₂₇ClN₆O₃Si
• Molecular Weight: 499.044
• Mol file: 1260168-98-6.mol

Synonyms:N-(5-(5-chloro-2-methoxyphenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide

Chemical Property of N-(5-(5-chloro-2-methoxyphenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(5-(5-chloro-2-methoxyphenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide

There total 6 articles about N-(5-(5-chloro-2-methoxyphenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidine-3-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: 84.0%

3-(5-chloro-2-methoxyphenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-4-amine (1260168-97-5) + pyrazolo[1,5-a] pyrimidine-3-carboxylic acid (25940-35-6) → N-(5-(5-chloro-2-methoxyphenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide (1260168-98-6)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; ((3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V); dmap; In N,N-dimethyl-formamide; at 40 ℃; for 1.5h;

Reference yield: 84.0%

5-(5-chloro-2-methoxyphenyl)-1-((2-(trimethylsilyl)ethoxy)-methyl)-1H-pyrazol-4-amine (1403963-78-9) + pyrazolo[1,5-a] pyrimidine-3-carboxylic acid (25940-35-6) → N-(5-(5-chloro-2-methoxyphenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide (1260168-98-6)

Guidance literature:

With dmap; N-ethyl-N,N-diisopropylamine; ((3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V); In N,N-dimethyl-formamide; at 40 ℃; for 24h;

DOI:10.1016/j.bmcl.2019.04.008

Reference yield:

(2-trimethylethylsilylethoxy)methyl chloride (76513-69-4) → N-(5-(5-chloro-2-methoxyphenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide (1260168-98-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 20 °C / Cooling with ice

1.2: 1.5 h / 20 °C

2.1: potassium carbonate; Trimethylacetic acid / palladium diacetate; catacxium A / N,N-dimethyl acetamide / 6 h / 120 °C / Inert atmosphere

3.1: ethanol; ammonium chloride / iron / water / 1.5 h / 75 °C

4.1: N-ethyl-N,N-diisopropylamine; ((3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V) / dmap / N,N-dimethyl-formamide / 1.5 h / 40 °C

With ethanol; sodium hydride; potassium carbonate; ammonium chloride; N-ethyl-N,N-diisopropylamine; ((3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V); Trimethylacetic acid; dmap; palladium diacetate; iron; catacxium A; In tetrahydrofuran; N,N-dimethyl acetamide; water; N,N-dimethyl-formamide; mineral oil;

upstream raw materials:

(2-trimethylethylsilylethoxy)methyl chloride

3-(5-chloro-2-methoxyphenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-4-amine

pyrazolo[1,5-a] pyrimidine-3-carboxylic acid

4-nitro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazole

Downstream raw materials:

N-(5-(5-chloro-2-methoxyphenyl)-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide

N-(3-(5-chloro-2-methoxyphenyl)-1-(2-morpholinoethyl)-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide

N-(5-(5-chloro-2-methoxyphenyl)-1-(2-morpholinoethyl)-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide

N-(3-(5-chloro-2-methoxyphenyl)-1-(3-methylbut-2-enyl)-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide