5-[(2-fluoro-3,5-dimethoxyphenyl)ethynyl]-N-{3-methoxy-4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl}pyrimidin-2-amine

Base Information

• Chemical Name: 5-[(2-fluoro-3,5-dimethoxyphenyl)ethynyl]-N-{3-methoxy-4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl}pyrimidin-2-amine
• CAS No.: 1453207-90-3
• Molecular Formula: C₃₁H₃₇FN₆O₃
• Molecular Weight: 560.672
• Mol file: 1453207-90-3.mol

Synonyms:5-[(2-fluoro-3,5-dimethoxyphenyl)ethynyl]-N-{3-methoxy-4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl}pyrimidin-2-amine

Chemical Property of 5-[(2-fluoro-3,5-dimethoxyphenyl)ethynyl]-N-{3-methoxy-4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl}pyrimidin-2-amine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-[(2-fluoro-3,5-dimethoxyphenyl)ethynyl]-N-{3-methoxy-4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl}pyrimidin-2-amine

There total 4 articles about 5-[(2-fluoro-3,5-dimethoxyphenyl)ethynyl]-N-{3-methoxy-4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl}pyrimidin-2-amine 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: 55.0%

5-iodo-N-{3-methoxy-4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl}pyrimidin-2-amine (1453211-47-6) + 1-ethynyl-2-fluoro-3,5-dimethoxybenzene (1453211-50-1) → 5-[(2-fluoro-3,5-dimethoxyphenyl)ethynyl]-N-{3-methoxy-4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl}pyrimidin-2-amine (1453207-90-3)

Guidance literature:

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; N-ethyl-N,N-diisopropylamine; at 80 ℃; for 1h; Inert atmosphere;

DOI:10.1016/j.bmc.2021.116019

Reference yield:

1-Ethynyl-3,5-dimethoxy-benzene (171290-52-1) → 5-[(2-fluoro-3,5-dimethoxyphenyl)ethynyl]-N-{3-methoxy-4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl}pyrimidin-2-amine (1453207-90-3)

Guidance literature:

Multi-step reaction with 2 steps

1: Selectfluor / acetonitrile / 96 h / 20 °C / Cooling with ice

2: N-ethyl-N,N-diisopropylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; copper(l) iodide / 1 h / 80 °C / Inert atmosphere

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; Selectfluor; N-ethyl-N,N-diisopropylamine; In acetonitrile; 2: |Sonogashira Cross-Coupling;

DOI:10.1016/j.bmc.2021.116019

Reference yield:

3-methoxy-4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]aniline (1254058-34-8) → 5-[(2-fluoro-3,5-dimethoxyphenyl)ethynyl]-N-{3-methoxy-4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl}pyrimidin-2-amine (1453207-90-3)

Guidance literature:

Multi-step reaction with 2 steps

1: methanesulfonic acid / 3 h / 130 °C / Microwave irradiation

2: N-ethyl-N,N-diisopropylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; copper(l) iodide / 1 h / 80 °C / Inert atmosphere

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; methanesulfonic acid; N-ethyl-N,N-diisopropylamine; 2: |Sonogashira Cross-Coupling;

DOI:10.1016/j.bmc.2021.116019

upstream raw materials:

5-iodo-N-{3-methoxy-4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl}pyrimidin-2-amine

1-ethynyl-2-fluoro-3,5-dimethoxybenzene

3-methoxy-4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]aniline

1-Ethynyl-3,5-dimethoxy-benzene

Downstream raw materials:

5-[2-(2-fluoro-3,5-dimethoxyphenyl)ethyl]-N-{3-methoxy-4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl}pyrimidin-2-amine