4-[4-Chloro-2-[2-(4-fluoro-1H-pyrazol-1-yl)ethoxy]-6-methylphenyl]-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-amine

Base Information

• Chemical Name: 4-[4-Chloro-2-[2-(4-fluoro-1H-pyrazol-1-yl)ethoxy]-6-methylphenyl]-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-amine
• CAS No.: 1207961-60-1
• Molecular Formula: C₁₈H₁₈ClFN₆O
• Molecular Weight: 388.832
• DSSTox Substance ID: DTXSID901107147
• Mol file: 1207961-60-1.mol

Synonyms:SCHEMBL1935237;DTXSID901107147;1207961-60-1;4-[4-Chloro-2-[2-(4-fluoro-1H-pyrazol-1-yl)ethoxy]-6-methylphenyl]-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-amine

Chemical Property of 4-[4-Chloro-2-[2-(4-fluoro-1H-pyrazol-1-yl)ethoxy]-6-methylphenyl]-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-amine

Chemical Property:

• XLogP3: 1.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 5
• Exact Mass: 388.1214651
• Heavy Atom Count: 27
• Complexity: 505

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=CC(=CC(=C1C2=NC(=NC3=C2CNC3)N)OCCN4C=C(C=N4)F)Cl

Technology Process of 4-[4-Chloro-2-[2-(4-fluoro-1H-pyrazol-1-yl)ethoxy]-6-methylphenyl]-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-amine

There total 17 articles about 4-[4-Chloro-2-[2-(4-fluoro-1H-pyrazol-1-yl)ethoxy]-6-methylphenyl]-6,7-dihydro-5H-pyrrolo[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:

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 (1207961-61-2) → 4-{4-chloro-2-[2-(4-fluoro-pyrazol-1-yl)-ethoxy]-6-methyl-phenyl}-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-ylamine (1207961-60-1)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; methanol; at 20 ℃; for 12h;

Reference yield:

5-chloro-2-iodo-1-methyl-3-nitrobenzene (1150617-61-0) → 4-{4-chloro-2-[2-(4-fluoro-pyrazol-1-yl)-ethoxy]-6-methyl-phenyl}-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-ylamine (1207961-60-1)

Guidance literature:

Multi-step reaction with 8 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

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

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

With hydrogenchloride; 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; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; 6.1: Suzuki coupling;

DOI:10.1021/jm200128m

Reference yield:

5-chloro-2-iodo-3-methylphenol (1150617-66-5) → 4-{4-chloro-2-[2-(4-fluoro-pyrazol-1-yl)-ethoxy]-6-methyl-phenyl}-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-ylamine (1207961-60-1)

Guidance literature:

Multi-step reaction with 6 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

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 bis[bis(diphenylphosphino)ferrocene] dichloride; boron tribromide; sodium carbonate; potassium carbonate; triethylamine; In 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; 4.1: Suzuki coupling;

DOI:10.1021/jm200128m

upstream raw materials:

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

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

5-chloro-2-iodo-3-methylphenylamine

5-chloro-2-iodo-3-methylphenol

Downstream raw materials:

2-amino-N-bicyclo[1.1.1]pent-1-yl-4-{4-chloro-2-[2-(4-fluoro-1H-pyrazol-1-yl)ethoxy]-6-methylphenyl}-5,7-dihydro-6H-pyrrolo[3,4-d]pyrimidine-6-carboxamide

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