N-(2-ethoxy-4-(1-methyl-1H-pyrazol-4-yl)phenyl)-8-(1-methyl-1H-pyrazol-4-yl)pyrido[3,4-d]pyrimidin-2-amine

Base Information

• Chemical Name: N-(2-ethoxy-4-(1-methyl-1H-pyrazol-4-yl)phenyl)-8-(1-methyl-1H-pyrazol-4-yl)pyrido[3,4-d]pyrimidin-2-amine
• CAS No.: 1578244-57-1
• Molecular Formula: C₂₃H₂₂N₈O
• Molecular Weight: 426.481

Synonyms:N-(2-ethoxy-4-(1-methyl-1H-pyrazol-4-yl)phenyl)-8-(1-methyl-1H-pyrazol-4-yl)pyrido[3,4-d]pyrimidin-2-amine

Chemical Property of N-(2-ethoxy-4-(1-methyl-1H-pyrazol-4-yl)phenyl)-8-(1-methyl-1H-pyrazol-4-yl)pyrido[3,4-d]pyrimidin-2-amine

Chemical Property:

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Technology Process of N-(2-ethoxy-4-(1-methyl-1H-pyrazol-4-yl)phenyl)-8-(1-methyl-1H-pyrazol-4-yl)pyrido[3,4-d]pyrimidin-2-amine

There total 6 articles about N-(2-ethoxy-4-(1-methyl-1H-pyrazol-4-yl)phenyl)-8-(1-methyl-1H-pyrazol-4-yl)pyrido[3,4-d]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: 40.0%

8-chloro-N-(2-ethoxy-4-(1-methyl-1H-pyrazol-4-yl)phenyl)pyrido[3,4-d]pyrimidin-2-amine (1578246-72-6) + 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (761446-44-0) → N-(2-ethoxy-4-(1-methyl-1H-pyrazol-4-yl)phenyl)-8-(1-methyl-1H-pyrazol-4-yl)pyrido[3,4-d]pyrimidin-2-amine (1578244-57-1)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; caesium carbonate; In 1,4-dioxane; water; at 100 ℃; for 0.5h; Microwave irradiation;

DOI:10.1021/acs.jmedchem.5b01811

Reference yield:

4-bromo-2-fluoronitrobenzene (321-23-3) → N-(2-ethoxy-4-(1-methyl-1H-pyrazol-4-yl)phenyl)-8-(1-methyl-1H-pyrazol-4-yl)pyrido[3,4-d]pyrimidin-2-amine (1578244-57-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.25 h / 0 °C

1.2: 18 h / 0 - 20 °C

2.1: tin(ll) chloride / ethanol / 2 h / 70 °C

3.1: sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; toluene; ethanol / 2.5 h / 80 °C

4.1: 1 h / 100 °C

5.1: sodium hydride / tetrahydrofuran; mineral oil / 0.25 h / 20 °C

5.2: 18 h / 0 - 20 °C

5.3: 1 h

6.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; caesium carbonate / water; 1,4-dioxane / 0.5 h / 100 °C / Microwave irradiation

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium hydride; sodium carbonate; caesium carbonate; tin(ll) chloride; In tetrahydrofuran; 1,4-dioxane; ethanol; water; toluene; mineral oil; 3.1: |Suzuki Coupling / 6.1: |Suzuki Coupling;

DOI:10.1021/acs.jmedchem.5b01811

Reference yield:

4-bromo-2-ethoxy-aniline (57279-73-9) → N-(2-ethoxy-4-(1-methyl-1H-pyrazol-4-yl)phenyl)-8-(1-methyl-1H-pyrazol-4-yl)pyrido[3,4-d]pyrimidin-2-amine (1578244-57-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; toluene; ethanol / 2.5 h / 80 °C

2.1: 1 h / 100 °C

3.1: sodium hydride / tetrahydrofuran; mineral oil / 0.25 h / 20 °C

3.2: 18 h / 0 - 20 °C

3.3: 1 h

4.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; caesium carbonate / water; 1,4-dioxane / 0.5 h / 100 °C / Microwave irradiation

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium hydride; sodium carbonate; caesium carbonate; In tetrahydrofuran; 1,4-dioxane; ethanol; water; toluene; mineral oil; 1.1: |Suzuki Coupling / 4.1: |Suzuki Coupling;

DOI:10.1021/acs.jmedchem.5b01811

upstream raw materials:

4-bromo-2-ethoxy-aniline

2-ethoxy-4-(1-methyl-1H-pyrazol-4-yl)aniline

4-bromo-2-fluoronitrobenzene

N-(2-ethoxy-4-(1-methyl-1H-pyrazol-4-yl)phenyl)formamide

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