4-(4-thiophen-2-yl-4-hydroxypiperidino)-2-(N-ethyl-2-bromo-4-isopropylanilino)-6-methylpyrimidine

Base Information

• Chemical Name: 4-(4-thiophen-2-yl-4-hydroxypiperidino)-2-(N-ethyl-2-bromo-4-isopropylanilino)-6-methylpyrimidine
• CAS No.: 213923-80-9
• Molecular Formula: C₂₅H₃₁BrN₄OS
• Molecular Weight: 515.517

Synonyms:4-(4-thiophen-2-yl-4-hydroxypiperidino)-2-(N-ethyl-2-bromo-4-isopropylanilino)-6-methylpyrimidine

Chemical Property of 4-(4-thiophen-2-yl-4-hydroxypiperidino)-2-(N-ethyl-2-bromo-4-isopropylanilino)-6-methylpyrimidine

Chemical Property:

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Technology Process of 4-(4-thiophen-2-yl-4-hydroxypiperidino)-2-(N-ethyl-2-bromo-4-isopropylanilino)-6-methylpyrimidine

There total 6 articles about 4-(4-thiophen-2-yl-4-hydroxypiperidino)-2-(N-ethyl-2-bromo-4-isopropylanilino)-6-methylpyrimidine 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: 44.0%

thiophene (188290-36-0,8014-23-1,25233-34-5) + 4-(4-oxopiperidino)-2-(N-ethyl-2-bromo-4-isopropylanilino)-6-methylpyrimidine (213923-77-4) → 4-(4-thiophen-2-yl-4-hydroxypiperidino)-2-(N-ethyl-2-bromo-4-isopropylanilino)-6-methylpyrimidine (213923-80-9)

Guidance literature:

thiophene; With n-butyllithium; In tetrahydrofuran; hexane; at 5 ℃; for 0.333333h;

4-(4-oxopiperidino)-2-(N-ethyl-2-bromo-4-isopropylanilino)-6-methylpyrimidine; In tetrahydrofuran; hexane; at -15 - 20 ℃;

DOI:10.1016/S0968-0896(00)00045-6

Reference yield:

2,4-dichloro-6-methylpyrimidine (5424-21-5) → 4-(4-thiophen-2-yl-4-hydroxypiperidino)-2-(N-ethyl-2-bromo-4-isopropylanilino)-6-methylpyrimidine (213923-80-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 79 percent / diisopropylethylamine / ethanol / 0 - 20 °C

2.1: 78 percent / diisopropylethylamine / ethane-1,2-diol / 1.5 h / Heating

3.1: NaH / dimethylformamide / 0.5 h / 20 °C

3.2: 76 percent / dimethylformamide / 15 h / 20 °C

4.1: 90 percent / aq. HCl / tetrahydrofuran / 6 h / 20 °C

5.1: n-BuLi / hexane; tetrahydrofuran / 0.33 h / 5 °C

5.2: 44 percent / tetrahydrofuran; hexane / -15 - 20 °C

With hydrogenchloride; n-butyllithium; sodium hydride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; ethanol; hexane; ethylene glycol; N,N-dimethyl-formamide; 1.1: Substitution / 2.1: Substitution / 3.1: deprotonation / 3.2: Alkylation / 4.1: Hydrolysis / 5.1: Metallation / 5.2: Addition;

DOI:10.1016/S0968-0896(00)00045-6

Reference yield:

4,4-ethylenedioxy-piperidine (177-11-7) → 4-(4-thiophen-2-yl-4-hydroxypiperidino)-2-(N-ethyl-2-bromo-4-isopropylanilino)-6-methylpyrimidine (213923-80-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 79 percent / diisopropylethylamine / ethanol / 0 - 20 °C

2.1: 78 percent / diisopropylethylamine / ethane-1,2-diol / 1.5 h / Heating

3.1: NaH / dimethylformamide / 0.5 h / 20 °C

3.2: 76 percent / dimethylformamide / 15 h / 20 °C

4.1: 90 percent / aq. HCl / tetrahydrofuran / 6 h / 20 °C

5.1: n-BuLi / hexane; tetrahydrofuran / 0.33 h / 5 °C

5.2: 44 percent / tetrahydrofuran; hexane / -15 - 20 °C

With hydrogenchloride; n-butyllithium; sodium hydride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; ethanol; hexane; ethylene glycol; N,N-dimethyl-formamide; 1.1: Substitution / 2.1: Substitution / 3.1: deprotonation / 3.2: Alkylation / 4.1: Hydrolysis / 5.1: Metallation / 5.2: Addition;

DOI:10.1016/S0968-0896(00)00045-6

upstream raw materials:

thiophene

4-(4-oxopiperidino)-2-(N-ethyl-2-bromo-4-isopropylanilino)-6-methylpyrimidine

2,4-dichloro-6-methylpyrimidine

4,4-ethylenedioxy-piperidine

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