tert-butyl 4-(4-((4-((2-(2-methoxy-2-oxoethyl)-5-methylphenyl)ethynyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)piperidine-1-carboxylate

Base Information

• Chemical Name: tert-butyl 4-(4-((4-((2-(2-methoxy-2-oxoethyl)-5-methylphenyl)ethynyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)piperidine-1-carboxylate
• CAS No.: 1566584-96-0
• Molecular Formula: C₃₃H₃₅F₃N₄O₄
• Molecular Weight: 608.661

Synonyms:tert-butyl 4-(4-((4-((2-(2-methoxy-2-oxoethyl)-5-methylphenyl)ethynyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)piperidine-1-carboxylate

Chemical Property of tert-butyl 4-(4-((4-((2-(2-methoxy-2-oxoethyl)-5-methylphenyl)ethynyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)piperidine-1-carboxylate

Chemical Property:

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Technology Process of tert-butyl 4-(4-((4-((2-(2-methoxy-2-oxoethyl)-5-methylphenyl)ethynyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)piperidine-1-carboxylate

There total 7 articles about tert-butyl 4-(4-((4-((2-(2-methoxy-2-oxoethyl)-5-methylphenyl)ethynyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)piperidine-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: 30.0%

tert-butyl 4-(4-((4-chloro-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)piperidine-1-carboxylate (1383682-52-7) + methyl 2-(2-ethynyl-4-methylphenyl)acetate (1566584-95-9) → tert-butyl 4-(4-((4-((2-(2-methoxy-2-oxoethyl)-5-methylphenyl)ethynyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)piperidine-1-carboxylate (1566584-96-0)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine; In N,N-dimethyl-formamide; at 120 ℃; for 0.25h; Microwave irradiation;

Reference yield:

2-bromo-4-methylbenzoic acid (7697-27-0) → tert-butyl 4-(4-((4-((2-(2-methoxy-2-oxoethyl)-5-methylphenyl)ethynyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)piperidine-1-carboxylate (1566584-96-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: oxalyl dichloride / tetrahydrofuran; N,N-dimethyl-formamide / 0.5 h / 20 °C / Inert atmosphere

1.2: 1 h / 0 - 20 °C / Inert atmosphere

2.1: triethylamine; silver benzoate / tetrahydrofuran / 2 h / 20 °C

3.1: copper(l) iodide; tri tert-butylphosphoniumtetrafluoroborate; triethylamine; bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 17 h / 70 °C

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran; dichloromethane / 0.08 h / 0 - 20 °C

5.1: copper(l) iodide; triethylamine; triphenylphosphine; bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 0.25 h / 120 °C / Microwave irradiation

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; oxalyl dichloride; tetrabutyl ammonium fluoride; silver benzoate; triethylamine; triphenylphosphine; tri tert-butylphosphoniumtetrafluoroborate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

Reference yield:

methyl 2-(4-methyl-2-((triethylsilyl)ethynyl)phenyl)acetate (1566584-94-8) → tert-butyl 4-(4-((4-((2-(2-methoxy-2-oxoethyl)-5-methylphenyl)ethynyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)piperidine-1-carboxylate (1566584-96-0)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrabutyl ammonium fluoride / tetrahydrofuran; dichloromethane / 0.08 h / 0 - 20 °C

2: copper(l) iodide; triethylamine; triphenylphosphine; bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 0.25 h / 120 °C / Microwave irradiation

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; tetrabutyl ammonium fluoride; triethylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

upstream raw materials:

2-bromo-4-methylbenzoic acid

1-(2-bromo-4-methylphenyl)-2-diazoethanone

methyl 2-(2-bromo-4-methylphenyl)acetate

methyl 2-(4-methyl-2-((triethylsilyl)ethynyl)phenyl)acetate

Downstream raw materials:

tert-butyl 4-(4-((4-(2-(2-methoxy-2-oxoethyl)-5-methylphenethyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)piperidine-1-carboxylate

2-(2-(2-(2-((4-(1-(tert-butoxycarbonyl)piperidin-4-yl)phenyl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)-4-methylphenyl)acetic acid

tert-butyl 4-(4-((4-(2-(2-amino-2-oxoethyl)-5-methylphenethyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)piperidine-1-carboxylate

2-(4-methyl-2-(2-(2-((4-(piperidine-4-yl)phenyl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)phenyl)acetamide

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