(E)-2-ethyl-5,7-dimethyl-3-(4-(3-(piperazin-1-yl)prop-1-enyl)benzyl)pyrazolo[1,5-a]pyrimidine

Base Information

• Chemical Name: (E)-2-ethyl-5,7-dimethyl-3-(4-(3-(piperazin-1-yl)prop-1-enyl)benzyl)pyrazolo[1,5-a]pyrimidine
• CAS No.: 1401728-34-4
• Molecular Formula: C₂₄H₃₁N₅
• Molecular Weight: 389.544
• Mol file: 1401728-34-4.mol

Synonyms:(E)-2-ethyl-5,7-dimethyl-3-(4-(3-(piperazin-1-yl)prop-1-enyl)benzyl)pyrazolo[1,5-a]pyrimidine

Chemical Property of (E)-2-ethyl-5,7-dimethyl-3-(4-(3-(piperazin-1-yl)prop-1-enyl)benzyl)pyrazolo[1,5-a]pyrimidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-2-ethyl-5,7-dimethyl-3-(4-(3-(piperazin-1-yl)prop-1-enyl)benzyl)pyrazolo[1,5-a]pyrimidine

There total 7 articles about (E)-2-ethyl-5,7-dimethyl-3-(4-(3-(piperazin-1-yl)prop-1-enyl)benzyl)pyrazolo[1,5-a]pyrimidine 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: 99.0%

(E)-tert-butyl 4-(3-(4-((2-ethyl-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)methyl)phenyl)allyl)piperazine-1-carboxylate → (E)-2-ethyl-5,7-dimethyl-3-(4-(3-(piperazin-1-yl)prop-1-enyl)benzyl)pyrazolo[1,5-a]pyrimidine (1401728-34-4)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; at 20 ℃; for 5h; Inert atmosphere;

DOI:10.1021/acs.jmedchem.6b01703

Reference yield:

3-(4-Bromo-phenyl)-propionitrile (57775-08-3) → (E)-2-ethyl-5,7-dimethyl-3-(4-(3-(piperazin-1-yl)prop-1-enyl)benzyl)pyrazolo[1,5-a]pyrimidine (1401728-34-4)

Guidance literature:

Multi-step reaction with 7 steps

1.1: potassium 2-methylbutan-2-olate / tetrahydrofuran; toluene / 0.33 h / 20 °C / Inert atmosphere

2.1: hydrazine hydrate; acetic acid / ethanol / 0.25 h / 140 °C / Inert atmosphere; Microwave irradiation

2.2: 0.5 h / 160 °C / Inert atmosphere; Microwave irradiation

3.1: trifluoroacetic acid / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere

4.1: N-Methyldicyclohexylamine; bis(tri-t-butylphosphine)palladium⁽⁰⁾ / 1,4-dioxane / 0.25 h / 130 °C / Inert atmosphere; Microwave irradiation

5.1: diisobutylaluminium hydride / dichloromethane; toluene / 3 h / -78 °C / Inert atmosphere

6.1: N-ethyl-N,N-diisopropylamine; (cyanomethyl)trimethyl-phosphonium iodide / 3 h / Inert atmosphere

7.1: hydrogenchloride / 1,4-dioxane / 5 h / 20 °C / Inert atmosphere

With hydrogenchloride; bis(tri-t-butylphosphine)palladium⁽⁰⁾; hydrazine hydrate; N-Methyldicyclohexylamine; diisobutylaluminium hydride; potassium 2-methylbutan-2-olate; acetic acid; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; (cyanomethyl)trimethyl-phosphonium iodide; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; toluene; 4.1: |Heck Reaction;

DOI:10.1021/acs.jmedchem.6b01703

Reference yield:

(E)-3-[4-(2-ethyl-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-ylmethyl)phenyl]acrylic acid methyl ester (1401728-64-0) → (E)-2-ethyl-5,7-dimethyl-3-(4-(3-(piperazin-1-yl)prop-1-enyl)benzyl)pyrazolo[1,5-a]pyrimidine (1401728-34-4)

Guidance literature:

Multi-step reaction with 3 steps

1: diisobutylaluminium hydride / dichloromethane; toluene / 3 h / -78 °C / Inert atmosphere

2: N-ethyl-N,N-diisopropylamine; (cyanomethyl)trimethyl-phosphonium iodide / 3 h / Inert atmosphere

3: hydrogenchloride / 1,4-dioxane / 5 h / 20 °C / Inert atmosphere

With hydrogenchloride; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; (cyanomethyl)trimethyl-phosphonium iodide; In 1,4-dioxane; dichloromethane; toluene;

DOI:10.1021/acs.jmedchem.6b01703

upstream raw materials:

3-(4-Bromo-phenyl)-propionitrile

2-(4-bromobenzyl)-3-oxopentanenitrile

4-(4-bromobenzyl)-5-ethyl-2H-pyrazol-3-ylamine

(E)-3-[4-(2-ethyl-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-ylmethyl)phenyl]acrylic acid methyl ester

Downstream raw materials:

C₃₃H₅₁N₅O₂Si

(R)-3-(4-{(E)-3-[4-(2-ethyl-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-ylmethyl)phenyl]allyl}piperazin-1-yl)propane-1,2-diol