N⁴-(3-chlorophenyl)-N⁶-(2-(morpholin-4-yl)ethyl)-1-(2-phenylethyl)-1H-pyrazolo[3,4-d]pyrimidine-4,6-diamine

Base Information

• Chemical Name: N⁴-(3-chlorophenyl)-N⁶-(2-(morpholin-4-yl)ethyl)-1-(2-phenylethyl)-1H-pyrazolo[3,4-d]pyrimidine-4,6-diamine
• CAS No.: 1583284-96-1
• Molecular Formula: C₂₅H₂₈ClN₇O
• Molecular Weight: 477.997

Synonyms:N⁴-(3-chlorophenyl)-N⁶-(2-(morpholin-4-yl)ethyl)-1-(2-phenylethyl)-1H-pyrazolo[3,4-d]pyrimidine-4,6-diamine

Chemical Property of N⁴-(3-chlorophenyl)-N⁶-(2-(morpholin-4-yl)ethyl)-1-(2-phenylethyl)-1H-pyrazolo[3,4-d]pyrimidine-4,6-diamine

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Technology Process of N⁴-(3-chlorophenyl)-N⁶-(2-(morpholin-4-yl)ethyl)-1-(2-phenylethyl)-1H-pyrazolo[3,4-d]pyrimidine-4,6-diamine

There total 4 articles about N⁴-(3-chlorophenyl)-N⁶-(2-(morpholin-4-yl)ethyl)-1-(2-phenylethyl)-1H-pyrazolo[3,4-d]pyrimidine-4,6-diamine 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: 89.0%

4-(2-AMINOETHYL)MORPHOLINE (2038-03-1) + N-(3-chlorophenyl)-6-(methylthio)-1-(2-phenylethyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (1338789-23-3) → N4-(3-chlorophenyl)-N6-(2-(morpholin-4-yl)ethyl)-1-(2-phenylethyl)-1H-pyrazolo[3,4-d]pyrimidine-4,6-diamine (1583284-96-1)

Guidance literature:

N-(3-chlorophenyl)-6-(methylthio)-1-(2-phenylethyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine; With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20 ℃; for 2h; Inert atmosphere;

4-(2-AMINOETHYL)MORPHOLINE; In tetrahydrofuran; at 40 ℃; for 12h; Inert atmosphere;

DOI:10.1021/co500004e

Reference yield:

4,6-dichloro-2-methylsulfanylpyrimidine-5-carboxyaldehyde (33097-11-9) → N4-(3-chlorophenyl)-N6-(2-(morpholin-4-yl)ethyl)-1-(2-phenylethyl)-1H-pyrazolo[3,4-d]pyrimidine-4,6-diamine (1583284-96-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: triethylamine; hydrazine hydrate / 1,4-dioxane / 5 h / 20 °C

2.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 4 - 100 °C / Cooling with ice; Inert atmosphere; Microwave irradiation

3.1: ethanol / 12 h / Reflux; Inert atmosphere

4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 20 °C / Inert atmosphere

4.2: 12 h / 40 °C / Inert atmosphere

With di-isopropyl azodicarboxylate; hydrazine hydrate; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane;

DOI:10.1021/co500004e

Reference yield:

4-chloro-6-methylmercapto-1H-pyrazolo[3,4-d]pyrimidine (85426-79-5) → N4-(3-chlorophenyl)-N6-(2-(morpholin-4-yl)ethyl)-1-(2-phenylethyl)-1H-pyrazolo[3,4-d]pyrimidine-4,6-diamine (1583284-96-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 4 - 100 °C / Cooling with ice; Inert atmosphere; Microwave irradiation

2.1: ethanol / 12 h / Reflux; Inert atmosphere

3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 20 °C / Inert atmosphere

3.2: 12 h / 40 °C / Inert atmosphere

With di-isopropyl azodicarboxylate; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; In tetrahydrofuran; ethanol; dichloromethane;

DOI:10.1021/co500004e

upstream raw materials:

4-(2-AMINOETHYL)MORPHOLINE

N-(3-chlorophenyl)-6-(methylthio)-1-(2-phenylethyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

4,6-dichloro-2-methylsulfanylpyrimidine-5-carboxyaldehyde

4-chloro-6-methylmercapto-1H-pyrazolo[3,4-d]pyrimidine

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