ethyl 4-(4-{5-[3-({[N-(tert-butoxycarbonyl)glycyl](methyl)amino}methyl)phenyl]pyrimidin-2-yl}piperazin-1-yl)benzoate

Base Information

• Chemical Name: ethyl 4-(4-{5-[3-({[N-(tert-butoxycarbonyl)glycyl](methyl)amino}methyl)phenyl]pyrimidin-2-yl}piperazin-1-yl)benzoate
• CAS No.: 1279027-50-7
• Molecular Formula: C₃₂H₄₀N₆O₅
• Molecular Weight: 588.707
• Mol file: 1279027-50-7.mol

Synonyms:ethyl 4-(4-{5-[3-({[N-(tert-butoxycarbonyl)glycyl](methyl)amino}methyl)phenyl]pyrimidin-2-yl}piperazin-1-yl)benzoate

Chemical Property of ethyl 4-(4-{5-[3-({[N-(tert-butoxycarbonyl)glycyl](methyl)amino}methyl)phenyl]pyrimidin-2-yl}piperazin-1-yl)benzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 4-(4-{5-[3-({[N-(tert-butoxycarbonyl)glycyl](methyl)amino}methyl)phenyl]pyrimidin-2-yl}piperazin-1-yl)benzoate

There total 3 articles about ethyl 4-(4-{5-[3-({[N-(tert-butoxycarbonyl)glycyl](methyl)amino}methyl)phenyl]pyrimidin-2-yl}piperazin-1-yl)benzoate 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: 100.0%

tert-butyl (2-{[3-(2-chloropyrimidin-5-yl)benzyl](methyl)amino}-2-oxoethyl)carbamate (1279027-08-5) + ethyl 4-(piperazin-1-yl)benzoate (80518-57-6) → ethyl 4-(4-{5-[3-({[N-(tert-butoxycarbonyl)glycyl](methyl)amino}methyl)phenyl]pyrimidin-2-yl}piperazin-1-yl)benzoate (1279027-50-7)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 60 ℃;

DOI:10.1016/j.bmc.2017.05.059

Reference yield:

tert-butyl (2-{methyl[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl]amino}-2-oxoethyl)carbamate (1279027-31-4) → ethyl 4-(4-{5-[3-({[N-(tert-butoxycarbonyl)glycyl](methyl)amino}methyl)phenyl]pyrimidin-2-yl}piperazin-1-yl)benzoate (1279027-50-7)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,2-dimethoxyethane; water / 24 h / Inert atmosphere; Heating

2: potassium carbonate / N,N-dimethyl-formamide / 60 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; potassium carbonate; In 1,2-dimethoxyethane; water; N,N-dimethyl-formamide; 1: |Suzuki-Miyaura Coupling;

DOI:10.1016/j.bmc.2017.05.059

Reference yield:

tert-butyl {2-[(3-bromobenzyl)(methyl)amino]-2-oxoethyl}carbamate (1279027-03-0) → ethyl 4-(4-{5-[3-({[N-(tert-butoxycarbonyl)glycyl](methyl)amino}methyl)phenyl]pyrimidin-2-yl}piperazin-1-yl)benzoate (1279027-50-7)

Guidance literature:

Multi-step reaction with 3 steps

1: potassium acetate; bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane / 18 h / 80 °C / Inert atmosphere

2: sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,2-dimethoxyethane; water / 24 h / Inert atmosphere; Heating

3: potassium carbonate / N,N-dimethyl-formamide / 60 °C

With bis-triphenylphosphine-palladium(II) chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium acetate; sodium carbonate; potassium carbonate; In 1,4-dioxane; 1,2-dimethoxyethane; water; N,N-dimethyl-formamide; 1: |Miyaura Borylation Reaction / 2: |Suzuki-Miyaura Coupling;

DOI:10.1016/j.bmc.2017.05.059

upstream raw materials:

tert-butyl (2-{methyl[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl]amino}-2-oxoethyl)carbamate

tert-butyl {2-[(3-bromobenzyl)(methyl)amino]-2-oxoethyl}carbamate

tert-butyl (2-{[3-(2-chloropyrimidin-5-yl)benzyl](methyl)amino}-2-oxoethyl)carbamate

ethyl 4-(piperazin-1-yl)benzoate

Downstream raw materials:

4-(4-{5-[3-({[N-(tert-butoxycarbonyl)glycyl](methyl)amino}methyl)phenyl]pyrimidin-2-yl}piperazin-1-yl)benzoic acid