2-amino-4-[2,4-dichloro-6-(2-chloroethoxy)-phenyl]-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: 2-amino-4-[2,4-dichloro-6-(2-chloroethoxy)-phenyl]-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carboxylic acid tert-butyl ester
• CAS No.: 1303416-50-3
• Molecular Formula: C₁₉H₂₁Cl₃N₄O₃
• Molecular Weight: 459.76

Synonyms:2-amino-4-[2,4-dichloro-6-(2-chloroethoxy)-phenyl]-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carboxylic acid tert-butyl ester

Chemical Property of 2-amino-4-[2,4-dichloro-6-(2-chloroethoxy)-phenyl]-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carboxylic acid tert-butyl ester

Chemical Property:

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Technology Process of 2-amino-4-[2,4-dichloro-6-(2-chloroethoxy)-phenyl]-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carboxylic acid tert-butyl ester

There total 11 articles about 2-amino-4-[2,4-dichloro-6-(2-chloroethoxy)-phenyl]-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carboxylic acid tert-butyl ester 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: 67.4%

2-amino-4-(2,4-dichloro-6-hydroxyphenyl)-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carboxylic acid tert-butyl ester (1046861-34-0) + 1-Bromo-2-chloroethane (107-04-0) → 2-amino-4-[2,4-dichloro-6-(2-chloroethoxy)-phenyl]-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carboxylic acid tert-butyl ester (1303416-50-3)

Guidance literature:

With caesium carbonate; In dimethyl sulfoxide; at 70 ℃; for 2h;

DOI:10.1021/jm200128m

Reference yield:

3,5-dichloro-2-iodophenol (1028332-19-5) → 2-amino-4-[2,4-dichloro-6-(2-chloroethoxy)-phenyl]-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carboxylic acid tert-butyl ester (1303416-50-3)

Guidance literature:

Multi-step reaction with 5 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: caesium carbonate / dimethyl sulfoxide / 2 h / 70 °C

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

DOI:10.1021/jm200128m

Reference yield:

1,5-dichloro-3-(ethoxymethoxy)-2-iodobenzene (1028332-20-8) → 2-amino-4-[2,4-dichloro-6-(2-chloroethoxy)-phenyl]-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carboxylic acid tert-butyl ester (1303416-50-3)

Guidance literature:

Multi-step reaction with 4 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: caesium carbonate / dimethyl sulfoxide / 2 h / 70 °C

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

DOI:10.1021/jm200128m

upstream raw materials:

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

2-amino-4-hydroxy-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carboxylic acid ethyl ester

Downstream raw materials:

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

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

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

2-amino-4-{2,4-dichloro-6-(2-ethylaminoethoxy)-phenyl}-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carboxylic acid cyclobutylamide

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