tert-butyl 3-(4-((4-(2-(2-amino-2-oxoethyl)phenethyl)-5-methylpyrimidin-2-yl)amino)-1H-pyrazole-1-yl)azetidine-1-carboxylate

Base Information

• Chemical Name: tert-butyl 3-(4-((4-(2-(2-amino-2-oxoethyl)phenethyl)-5-methylpyrimidin-2-yl)amino)-1H-pyrazole-1-yl)azetidine-1-carboxylate
• CAS No.: 1566585-48-5
• Molecular Formula: C₂₆H₃₃N₇O₃
• Molecular Weight: 491.593
• Mol file: 1566585-48-5.mol

Synonyms:

Chemical Property of tert-butyl 3-(4-((4-(2-(2-amino-2-oxoethyl)phenethyl)-5-methylpyrimidin-2-yl)amino)-1H-pyrazole-1-yl)azetidine-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl 3-(4-((4-(2-(2-amino-2-oxoethyl)phenethyl)-5-methylpyrimidin-2-yl)amino)-1H-pyrazole-1-yl)azetidine-1-carboxylate

There total 6 articles about tert-butyl 3-(4-((4-(2-(2-amino-2-oxoethyl)phenethyl)-5-methylpyrimidin-2-yl)amino)-1H-pyrazole-1-yl)azetidine-1-carboxylate 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: 19.0%

tert-butyl 3-(4-amino-1H-pyrazol-1-yl)azetidine-1-carboxylate (1029413-51-1) + 2-(2-(2-(2-chloro-5-methylpyrimidin-4-yl)ethyl)phenyl)acetamide (1566584-27-7) → tert-butyl 3-(4-((4-(2-(2-amino-2-oxoethyl)phenethyl)-5-methylpyrimidin-2-yl)amino)-1H-pyrazole-1-yl)azetidine-1-carboxylate (1566585-48-5)

Guidance literature:

With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; at 100 ℃; for 2.5h; Microwave irradiation;

Reference yield:

2-(2-((trimethylsilyl)ethynyl)phenyl)acetamide → tert-butyl 3-(4-((4-(2-(2-amino-2-oxoethyl)phenethyl)-5-methylpyrimidin-2-yl)amino)-1H-pyrazole-1-yl)azetidine-1-carboxylate (1566585-48-5)

Guidance literature:

Multi-step reaction with 4 steps

1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran; dichloromethane / 1 h / 5 °C

2: copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane / 0.33 h / 70 °C / Inert atmosphere

3: hydrogen; platinum(IV) oxide / N,N-dimethyl-formamide; methanol / 40 h

4: palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 2.5 h / 100 °C / Microwave irradiation

With platinum(IV) oxide; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; tetrabutyl ammonium fluoride; hydrogen; palladium diacetate; caesium carbonate; acetic acid; triethylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide;

Reference yield:

o-iodophenylacetic acid (18698-96-9) → tert-butyl 3-(4-((4-(2-(2-amino-2-oxoethyl)phenethyl)-5-methylpyrimidin-2-yl)amino)-1H-pyrazole-1-yl)azetidine-1-carboxylate (1566585-48-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: thionyl chloride / 3 h / 75 °C

1.2: 20 h / 60 °C

2.1: copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 3 h / 50 °C / Inert atmosphere

3.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran; dichloromethane / 1 h / 5 °C

4.1: copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane / 0.33 h / 70 °C / Inert atmosphere

5.1: hydrogen; platinum(IV) oxide / N,N-dimethyl-formamide; methanol / 40 h

6.1: palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 2.5 h / 100 °C / Microwave irradiation

With platinum(IV) oxide; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; thionyl chloride; tetrabutyl ammonium fluoride; hydrogen; palladium diacetate; caesium carbonate; acetic acid; triethylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide;

upstream raw materials:

tert-butyl 3-(4-amino-1H-pyrazol-1-yl)azetidine-1-carboxylate

2-(2-(2-(2-chloro-5-methylpyrimidin-4-yl)ethyl)phenyl)acetamide

o-iodophenylacetic acid

2-(2-ethynylphenyl)acetamide