4-{2,4-dichloro-6-[2-(4-chloropyrazol-1-yl)-ethoxy]-phenyl}-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-ylamine

Base Information

• Chemical Name: 4-{2,4-dichloro-6-[2-(4-chloropyrazol-1-yl)-ethoxy]-phenyl}-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-ylamine
• CAS No.: 1207961-41-8
• Molecular Formula: C₁₇H₁₅Cl₃N₆O
• Molecular Weight: 425.705

Synonyms:4-{2,4-dichloro-6-[2-(4-chloropyrazol-1-yl)-ethoxy]-phenyl}-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-ylamine

Chemical Property of 4-{2,4-dichloro-6-[2-(4-chloropyrazol-1-yl)-ethoxy]-phenyl}-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-ylamine

Chemical Property:

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Technology Process of 4-{2,4-dichloro-6-[2-(4-chloropyrazol-1-yl)-ethoxy]-phenyl}-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-ylamine

There total 13 articles about 4-{2,4-dichloro-6-[2-(4-chloropyrazol-1-yl)-ethoxy]-phenyl}-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-ylamine 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: 100.0%

2-amino-4-{2,4-dichloro-6-[2-(4-chloropyrazol-1-yl)-ethoxy]-phenyl}-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carboxylic acid tert-butyl ester (1207961-42-9) → 4-{2,4-dichloro-6-[2-(4-chloropyrazol-1-yl)-ethoxy]-phenyl}-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-ylamine (1207961-41-8)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; methanol; at 23 ℃; for 12h;

DOI:10.1021/jm200128m

Reference yield:

3,5-dichloro-2-iodophenol (1028332-19-5) → 4-{2,4-dichloro-6-[2-(4-chloropyrazol-1-yl)-ethoxy]-phenyl}-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-ylamine (1207961-41-8)

Guidance literature:

Multi-step reaction with 6 steps

1.1: potassium carbonate / N,N-dimethyl-formamide / 12 h / 20 °C

2.1: palladium diacetate; triethylamine; CyJohnPhos / 1,4-dioxane / 2 h / 80 °C / Inert atmosphere

3.1: boron tribromide / dichloromethane / 0.33 h / 0 °C / Inert atmosphere

3.2: Cooling

4.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / 1,4-dioxane; water / 0.67 h / 120 °C / Inert atmosphere; Microwave irradiation

5.1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 100 °C / Inert atmosphere

6.1: hydrogenchloride / 1,4-dioxane; methanol / 12 h / 23 °C

With hydrogenchloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; palladium diacetate; boron tribromide; sodium carbonate; potassium carbonate; triethylamine; CyJohnPhos; In 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide; 4.1: Suzuki coupling;

DOI:10.1021/jm200128m

Reference yield:

1,5-dichloro-3-(ethoxymethoxy)-2-iodobenzene (1028332-20-8) → 4-{2,4-dichloro-6-[2-(4-chloropyrazol-1-yl)-ethoxy]-phenyl}-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-ylamine (1207961-41-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: palladium diacetate; triethylamine; CyJohnPhos / 1,4-dioxane / 2 h / 80 °C / Inert atmosphere

2.1: boron tribromide / dichloromethane / 0.33 h / 0 °C / Inert atmosphere

2.2: Cooling

3.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / 1,4-dioxane; water / 0.67 h / 120 °C / Inert atmosphere; Microwave irradiation

4.1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 100 °C / Inert atmosphere

5.1: hydrogenchloride / 1,4-dioxane; methanol / 12 h / 23 °C

With hydrogenchloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; palladium diacetate; boron tribromide; sodium carbonate; potassium carbonate; triethylamine; CyJohnPhos; In 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide; 3.1: Suzuki coupling;

DOI:10.1021/jm200128m

upstream raw materials:

2-amino-4-{2,4-dichloro-6-[2-(4-chloropyrazol-1-yl)-ethoxy]-phenyl}-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carboxylic acid tert-butyl ester

3,5-dichloro-2-iodophenol

1,5-dichloro-3-(ethoxymethoxy)-2-iodobenzene

2-(2,4-dichloro-6-(ethoxymethoxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Downstream raw materials:

2-amino-4-{2,4-dichloro-6-[2-(4-chloropyrazol-1-yl)ethoxy]phenyl}-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carboxylic acid bicyclo[1.1.1]pent-1-ylamide

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