2-amino-4-(4-chloro-2-hydroxy-6-methylphenyl)-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: 2-amino-4-(4-chloro-2-hydroxy-6-methylphenyl)-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carboxylic acid tert-butyl ester
• CAS No.: 1207961-48-5
• Molecular Formula: C₁₈H₂₁ClN₄O₃
• Molecular Weight: 376.843

Synonyms:2-amino-4-(4-chloro-2-hydroxy-6-methylphenyl)-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carboxylic acid tert-butyl ester

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

Chemical Property:

Purity/Quality:

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

There total 12 articles about 2-amino-4-(4-chloro-2-hydroxy-6-methylphenyl)-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: 59.6%

2-amino-4-iodo-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carboxylic acid tert-butyl ester (1046861-23-7) + 4-chloro-2-hydroxy-6-methylphenylboronic acid (1207961-50-9) → 2-amino-4-(4-chloro-2-hydroxy-6-methylphenyl)-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carboxylic acid tert-butyl ester (1207961-48-5)

Guidance literature:

With sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,4-dioxane; water; at 120 ℃; for 0.666667h; microwave irradiation; Inert atmosphere;

Reference yield:

5-chloro-2-iodo-3-methylphenol (1150617-66-5) → 2-amino-4-(4-chloro-2-hydroxy-6-methylphenyl)-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carboxylic acid tert-butyl ester (1207961-48-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: potassium carbonate / acetonitrile / 12 h / 23 °C

2.1: palladium bis[bis(diphenylphosphino)ferrocene] dichloride; triethylamine / acetonitrile / 3 h / Reflux

3.1: boron tribromide / dichloromethane / 0.17 h / 0 °C

3.2: Cooling

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

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; palladium bis[bis(diphenylphosphino)ferrocene] dichloride; boron tribromide; sodium carbonate; potassium carbonate; triethylamine; In 1,4-dioxane; dichloromethane; water; acetonitrile; 4.1: Suzuki coupling;

DOI:10.1021/jm200128m

Reference yield:

5-chloro-2-iodo-1-methyl-3-nitrobenzene (1150617-61-0) → 2-amino-4-(4-chloro-2-hydroxy-6-methylphenyl)-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carboxylic acid tert-butyl ester (1207961-48-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: iron; ammonium chloride / ethanol; water / 0.5 h / Reflux

2.1: sulfuric acid; acetic acid; sodium nitrite / 0.5 h / 23 °C

2.2: Reflux

3.1: potassium carbonate / acetonitrile / 12 h / 23 °C

4.1: palladium bis[bis(diphenylphosphino)ferrocene] dichloride; triethylamine / acetonitrile / 3 h / Reflux

5.1: boron tribromide / dichloromethane / 0.17 h / 0 °C

5.2: Cooling

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

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; palladium bis[bis(diphenylphosphino)ferrocene] dichloride; sulfuric acid; boron tribromide; iron; sodium carbonate; potassium carbonate; ammonium chloride; acetic acid; triethylamine; sodium nitrite; In 1,4-dioxane; ethanol; dichloromethane; water; acetonitrile; 6.1: Suzuki coupling;

DOI:10.1021/jm200128m

upstream raw materials:

2-amino-4-iodo-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carboxylic acid tert-butyl ester

4-chloro-2-hydroxy-6-methylphenylboronic acid

5-chloro-2-iodo-1-methyl-3-nitrobenzene

5-chloro-2-iodo-3-methylphenylamine

Downstream raw materials:

C₂₃H₂₇ClN₆O₃

2-amino-4-{4-chloro-2-[2-(4-fluoro-pyrazol-1-yl)-ethoxy]-6-methyl-phenyl}-5,7-dihydro-pyrrolo[3,4-d]pyrimidine-6-carboxylic acid tert-butyl ester

2-amino-4-{4-chloro-2-[2-(4-fluoropyrazol-1-yl)ethoxy]-6-methylphenyl}-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carboxylic acid (2,2,2-trifluoroethyl)amide

2-amino-4-{4-chloro-2-[2-(4-fluoropyrazol-1-yl)ethoxy]-6-methylphenyl}-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carboxylic acid (2,2-difluoropropyl)amide

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