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

Base Information

• Chemical Name: (E)-3-[4-(2-ethyl-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-ylmethyl)phenyl]acrylic acid methyl ester
• CAS No.: 1401728-64-0
• Molecular Formula: C₂₁H₂₃N₃O₂
• Molecular Weight: 349.433
• Mol file: 1401728-64-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 4 articles about (E)-3-[4-(2-ethyl-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-ylmethyl)phenyl]acrylic acid methyl ester 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: 95.0%

3-(4-bromobenzyl)-2-ethyl-5,7-dimethylpyrazolo[1,5-a]pyrimidine (1401728-63-9) + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → (E)-3-[4-(2-ethyl-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-ylmethyl)phenyl]acrylic acid methyl ester (1401728-64-0)

Guidance literature:

With bis(tri-t-butylphosphine)palladium⁽⁰⁾; N-Methyldicyclohexylamine; In 1,4-dioxane; at 130 ℃; for 0.25h; Inert atmosphere; Microwave irradiation;

DOI:10.1021/acs.jmedchem.6b01703

Reference yield:

3-(4-Bromo-phenyl)-propionitrile (57775-08-3) → (E)-3-[4-(2-ethyl-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-ylmethyl)phenyl]acrylic acid methyl ester (1401728-64-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: potassium 2-methylbutan-2-olate / tetrahydrofuran; toluene / 20 °C

1.2: 0.33 h / 20 °C

2.1: hydrazine hydrate / ethanol / 0.25 h / 140 °C / Microwave irradiation

3.1: trifluoroacetic acid / 1,4-dioxane / 20 °C

4.1: bis(tri-t-butylphosphine)palladium ⁽⁰⁾; N-Methyldicyclohexylamine / 1,4-dioxane / 0.08 h / 130 °C / Microwave irradiation

With bis(tri-t-butylphosphine)palladium ⁽⁰⁾; N-Methyldicyclohexylamine; potassium 2-methylbutan-2-olate; hydrazine hydrate; trifluoroacetic acid; In tetrahydrofuran; 1,4-dioxane; ethanol; toluene;

Reference yield:

2-(4-bromobenzyl)-3-oxopentanenitrile (1401728-61-7) → (E)-3-[4-(2-ethyl-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-ylmethyl)phenyl]acrylic acid methyl ester (1401728-64-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: acetic acid; hydrazine hydrate / ethanol / 0.25 h / 140 °C / Microwave irradiation

1.2: 160 °C

2.1: trifluoroacetic acid / 1,4-dioxane / 20 °C

3.1: bis(tri-t-butylphosphine)palladium ⁽⁰⁾; N-Methyldicyclohexylamine / 1,4-dioxane / 0.08 h / 130 °C / Microwave irradiation

With bis(tri-t-butylphosphine)palladium ⁽⁰⁾; N-Methyldicyclohexylamine; hydrazine hydrate; acetic acid; trifluoroacetic acid; In 1,4-dioxane; ethanol;

upstream raw materials:

2-(4-bromobenzyl)-3-oxopentanenitrile

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

3-(4-Bromo-phenyl)-propionitrile

3-(4-bromobenzyl)-2-ethyl-5,7-dimethylpyrazolo[1,5-a]pyrimidine

Downstream raw materials:

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

(E)-tert-butyl 4-(3-(4-((2-ethyl-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)methyl)phenyl)acryloyl)piperazine-1-carboxylate

tert-butyl 4-(3-(4-((2-ethyl-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)methyl)phenyl)propanoyl)piperazine-1-carboxylate

C₃₀H₄₁N₅O₃