5-chloro-N₂-(4-(1-(2,2-difluoroethyl)piperidin-4-yl)-2-isopropoxy-5-methylphenyl)-N₄-(2-(isopropylsulfonyl)phenyl)pyrimidine-2,4-diamine

Base Information

• Chemical Name: 5-chloro-N₂-(4-(1-(2,2-difluoroethyl)piperidin-4-yl)-2-isopropoxy-5-methylphenyl)-N₄-(2-(isopropylsulfonyl)phenyl)pyrimidine-2,4-diamine
• CAS No.: 1445895-08-8
• Molecular Formula: C₃₀H₃₈ClF₂N₅O₃S
• Molecular Weight: 622.179

Synonyms:5-chloro-N₂-(4-(1-(2,2-difluoroethyl)piperidin-4-yl)-2-isopropoxy-5-methylphenyl)-N₄-(2-(isopropylsulfonyl)phenyl)pyrimidine-2,4-diamine

Chemical Property of 5-chloro-N₂-(4-(1-(2,2-difluoroethyl)piperidin-4-yl)-2-isopropoxy-5-methylphenyl)-N₄-(2-(isopropylsulfonyl)phenyl)pyrimidine-2,4-diamine

Chemical Property:

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Technology Process of 5-chloro-N₂-(4-(1-(2,2-difluoroethyl)piperidin-4-yl)-2-isopropoxy-5-methylphenyl)-N₄-(2-(isopropylsulfonyl)phenyl)pyrimidine-2,4-diamine

There total 10 articles about 5-chloro-N₂-(4-(1-(2,2-difluoroethyl)piperidin-4-yl)-2-isopropoxy-5-methylphenyl)-N₄-(2-(isopropylsulfonyl)phenyl)pyrimidine-2,4-diamine 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: 5.0%

2-bromo-1,1-difluoroethane (359-07-9) + 5-chloro-N2-(2-isopropoxy-5-methyl-4-(piperidin-4-yl)phenyl)-N4-(2-(isopropylsulfonyl)phenyl)pyrimidine-2,4-diamine hydrochloride (1380575-43-8) → 5-chloro-N2-(4-(1-(2,2-difluoroethyl)piperidin-4-yl)-2-isopropoxy-5-methylphenyl)-N4-(2-(isopropylsulfonyl)phenyl)pyrimidine-2,4-diamine (1445895-08-8)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In ethanol; at 50 ℃;

DOI:10.1021/jm400402q

Reference yield:

1-amino-2-(isopropylsulphonyl)benzene (76697-50-2) → 5-chloro-N2-(4-(1-(2,2-difluoroethyl)piperidin-4-yl)-2-isopropoxy-5-methylphenyl)-N4-(2-(isopropylsulfonyl)phenyl)pyrimidine-2,4-diamine (1445895-08-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hydride / N,N-dimethyl-formamide; dimethyl sulfoxide / 0 °C

1.2: 0 - 20 °C

2.1: caesium carbonate; palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / tetrahydrofuran / 0.33 h / 150 °C / Inert atmosphere; Microwave irradiation

3.1: trifluoroacetic acid / dichloromethane / 0.75 h / 20 °C

4.1: N-ethyl-N,N-diisopropylamine / ethanol / 50 °C

With palladium diacetate; sodium hydride; caesium carbonate; N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; trifluoroacetic acid; In tetrahydrofuran; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; 2.1: |Buchwald-Hartwig Coupling;

DOI:10.1021/jm400402q

Reference yield:

1-chloro-5-fluoro-2-methyl-4-nitrobenzene (112108-73-3) → 5-chloro-N2-(4-(1-(2,2-difluoroethyl)piperidin-4-yl)-2-isopropoxy-5-methylphenyl)-N4-(2-(isopropylsulfonyl)phenyl)pyrimidine-2,4-diamine (1445895-08-8)

Guidance literature:

Multi-step reaction with 7 steps

1: caesium carbonate / 60 °C

2: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate / 1,4-dioxane; water / 0.33 h / 150 °C / Inert atmosphere; Microwave irradiation

3: acetic acid; trifluoroacetic acid; platinum(IV) oxide; hydrogen / 36 h / 760.05 Torr

4: triethylamine / dichloromethane / 0.5 h / 20 °C

5: caesium carbonate; palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / tetrahydrofuran / 0.33 h / 150 °C / Inert atmosphere; Microwave irradiation

6: trifluoroacetic acid / dichloromethane / 0.75 h / 20 °C

7: N-ethyl-N,N-diisopropylamine / ethanol / 50 °C

With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; platinum(IV) oxide; potassium phosphate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; hydrogen; palladium diacetate; caesium carbonate; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; trifluoroacetic acid; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; water; 2: |Suzuki Coupling / 5: |Buchwald-Hartwig Coupling;

DOI:10.1021/jm400402q

upstream raw materials:

2-bromo-1,1-difluoroethane

5-chloro-N²-(2-isopropoxy-5-methyl-4-(piperidin-4-yl)phenyl)-N⁴-(2-(isopropylsulfonyl)phenyl)pyrimidine-2,4-diamine hydrochloride

1-chloro-5-fluoro-2-methyl-4-nitrobenzene

1-chloro-2-methyl-4-nitro-5-(propan-2-yloxy)benzene

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