tert-butyl (2R,4r,6S)-4-((3,5-bis(trifluoromethyl)benzyl)(5-bromopyrimidin-2-yl)amino)-2,6-diethylpiperidine-1-carboxylate

Base Information

• Chemical Name: tert-butyl (2R,4r,6S)-4-((3,5-bis(trifluoromethyl)benzyl)(5-bromopyrimidin-2-yl)amino)-2,6-diethylpiperidine-1-carboxylate
• CAS No.: 1148129-86-5
• Molecular Formula: C₂₇H₃₃BrF₆N₄O₂
• Molecular Weight: 639.479
• Mol file: 1148129-86-5.mol

Synonyms:tert-butyl (2R,4r,6S)-4-((3,5-bis(trifluoromethyl)benzyl)(5-bromopyrimidin-2-yl)amino)-2,6-diethylpiperidine-1-carboxylate

Chemical Property of tert-butyl (2R,4r,6S)-4-((3,5-bis(trifluoromethyl)benzyl)(5-bromopyrimidin-2-yl)amino)-2,6-diethylpiperidine-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (2R,4r,6S)-4-((3,5-bis(trifluoromethyl)benzyl)(5-bromopyrimidin-2-yl)amino)-2,6-diethylpiperidine-1-carboxylate

There total 4 articles about tert-butyl (2R,4r,6S)-4-((3,5-bis(trifluoromethyl)benzyl)(5-bromopyrimidin-2-yl)amino)-2,6-diethylpiperidine-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: 86.0%

tert-butyl (2R,4r,6S)-4-((5-bromopyrimidin-2-yl)amino)-2,6-diethylpiperidine-1-carboxylate (1148130-20-4) + 3,5-bis(trifluoromethyl)benzyl bromide (32247-96-4) → tert-butyl (2R,4r,6S)-4-((3,5-bis(trifluoromethyl)benzyl)(5-bromopyrimidin-2-yl)amino)-2,6-diethylpiperidine-1-carboxylate (1148129-86-5)

Guidance literature:

tert-butyl (2R,4r,6S)-4-((5-bromopyrimidin-2-yl)amino)-2,6-diethylpiperidine-1-carboxylate; With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 1h;

3,5-bis(trifluoromethyl)benzyl bromide; In N,N-dimethyl-formamide; at 0 - 20 ℃;

Reference yield:

tert-butyl (2R,6S)-2,6-diethyl-4-oxopiperidine-1-carboxylate (1003843-30-8) → tert-butyl (2R,4r,6S)-4-((3,5-bis(trifluoromethyl)benzyl)(5-bromopyrimidin-2-yl)amino)-2,6-diethylpiperidine-1-carboxylate (1148129-86-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: titanium(IV)isopropoxide / methanol / 20 °C / Inert atmosphere

1.2: 1 h / 20 °C / Inert atmosphere

2.1: palladium 10% on activated carbon; hydrogen / ethanol / 5 h / 55 °C

3.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 3.5 h / 120 °C / Inert atmosphere

4.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 0 °C / Inert atmosphere

4.2: 1 h / 20 °C / Inert atmosphere

With palladium 10% on activated carbon; hydrogen; titanium(IV)isopropoxide; sodium hydride; N-ethyl-N,N-diisopropylamine; In methanol; ethanol; N,N-dimethyl-formamide; mineral oil;

DOI:10.1021/acs.jmedchem.7b00900

Reference yield:

tert-butyl (2R,4r,6S)-4-amino-2,6-diethylpiperidine-1-carboxylate (1148130-19-1) → tert-butyl (2R,4r,6S)-4-((3,5-bis(trifluoromethyl)benzyl)(5-bromopyrimidin-2-yl)amino)-2,6-diethylpiperidine-1-carboxylate (1148129-86-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 3.5 h / 120 °C / Inert atmosphere

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 0 °C / Inert atmosphere

2.2: 1 h / 20 °C / Inert atmosphere

With sodium hydride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; mineral oil;

DOI:10.1021/acs.jmedchem.7b00900

upstream raw materials:

tert-butyl (2R,4r,6S)-4-((5-bromopyrimidin-2-yl)amino)-2,6-diethylpiperidine-1-carboxylate

3,5-bis(trifluoromethyl)benzyl bromide

tert-butyl (2R,4r,6S)-4-amino-2,6-diethylpiperidine-1-carboxylate

tert-butyl (2R,6S)-2,6-diethyl-4-oxopiperidine-1-carboxylate

Downstream raw materials:

tert-butyl (2R,4r,6S)-4-((3,5-bis(trifluoromethyl)benzyl)(5-(1-methyl-1H-pyrazol-4-yl)pyrimidin-2-yl)amino)-2,6-diethylpiperidine-1-carboxylate

tert-butyl (2R,4r,6S)-4-((3,5-bis(trifluoromethyl)benzyl)(5-morpholinopyrimidin-2-yl)amino)-2,6-diethylpiperidine-1-carboxylate

(1r,4r)-4-(methoxycarbonyl)-cyclohexyl (2R,4r,6S)-4-((3,5-bis(trifluoromethyl)benzyl)(5-(1-methyl-1H-pyrazol-4-yl)pyrimidin-2-yl)amino)-2,6-diethylpiperidine-1-carboxylate

N-(3,5-bis-(trifluoromethyl)benzyl)-N-((2R,4r,6S)-2,6-diethylpiperidin-4-yl)-5-(1-methyl-1H-pyrazol-4-yl)pyrimidin-2-amine