4-amino-6-(1-(6-fluoro-4-((S)-2-hydroxyethylsulfinyl)-3-phenylquinolin-2-yl)ethylamino)pyrimidine-5-carbonitrile

Base Information

• Chemical Name: 4-amino-6-(1-(6-fluoro-4-((S)-2-hydroxyethylsulfinyl)-3-phenylquinolin-2-yl)ethylamino)pyrimidine-5-carbonitrile
• CAS No.: 1259522-09-2
• Molecular Formula: C₂₄H₂₁FN₆O₂S
• Molecular Weight: 476.534

Synonyms:4-amino-6-(1-(6-fluoro-4-((S)-2-hydroxyethylsulfinyl)-3-phenylquinolin-2-yl)ethylamino)pyrimidine-5-carbonitrile

Chemical Property of 4-amino-6-(1-(6-fluoro-4-((S)-2-hydroxyethylsulfinyl)-3-phenylquinolin-2-yl)ethylamino)pyrimidine-5-carbonitrile

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of 4-amino-6-(1-(6-fluoro-4-((S)-2-hydroxyethylsulfinyl)-3-phenylquinolin-2-yl)ethylamino)pyrimidine-5-carbonitrile

There total 16 articles about 4-amino-6-(1-(6-fluoro-4-((S)-2-hydroxyethylsulfinyl)-3-phenylquinolin-2-yl)ethylamino)pyrimidine-5-carbonitrile 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-(2-(1-aminoethyl)-6-fluoro-3-phenylquinolin-4-ylsulfinyl)ethanol + 4-amino-6-chloropyrimidine-5-carbonitrile (60025-09-4) → 4-amino-6-(1-(6-fluoro-4-((S)-2-hydroxyethylsulfinyl)-3-phenylquinolin-2-yl)ethylamino)pyrimidine-5-carbonitrile (1259522-09-2) + 4-amino-6-(1-(6-fluoro-4-((R)-2-hydroxyethylsulfinyl)-3-phenylquinolin-2-yl)ethylamino)pyrimidine-5-carbonitrile (1259522-07-0)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In butan-1-ol; at 125 ℃; for 4h;

Reference yield:

4-fluoroaniline (371-40-4) → 4-amino-6-(1-(6-fluoro-4-((S)-2-hydroxyethylsulfinyl)-3-phenylquinolin-2-yl)ethylamino)pyrimidine-5-carbonitrile (1259522-09-2) + 4-amino-6-(1-(6-fluoro-4-((R)-2-hydroxyethylsulfinyl)-3-phenylquinolin-2-yl)ethylamino)pyrimidine-5-carbonitrile (1259522-07-0)

Guidance literature:

Multi-step reaction with 10 steps

1: trichlorophosphate / 60 °C

2: potassium carbonate; 1,1'-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex / tetrahydrofuran / 6 h / Reflux

3: N,N-dimethyl-formamide / 16 h / 100 °C

4: 1H-imidazole / N,N-dimethyl-formamide / 2 h

5: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 3 h / Reflux

6: N,N-dimethyl-formamide / 16 h / 60 °C

7: oxone / tetrahydrofuran; water / 16 h / 20 °C

8: hydrazine / ethanol / 0.5 h / 60 °C

9: butan-1-ol / 16 h / 100 °C

10: chiral AD column / Resolution of racemate

With 1H-imidazole; N-Bromosuccinimide; 1,1'-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex; potassium carbonate; hydrazine; trichlorophosphate; dibenzoyl peroxide; In tetrahydrofuran; tetrachloromethane; ethanol; water; N,N-dimethyl-formamide; butan-1-ol;

DOI:10.1016/j.bmcl.2015.01.001

Reference yield:

3-(4-fluorophenylamino)-3-oxo-2-phenylpropanoic acid (1259521-33-9) → 4-amino-6-(1-(6-fluoro-4-((S)-2-hydroxyethylsulfinyl)-3-phenylquinolin-2-yl)ethylamino)pyrimidine-5-carbonitrile (1259522-09-2) + 4-amino-6-(1-(6-fluoro-4-((R)-2-hydroxyethylsulfinyl)-3-phenylquinolin-2-yl)ethylamino)pyrimidine-5-carbonitrile (1259522-07-0)

Guidance literature:

Multi-step reaction with 11 steps

1: polyphosphoric acid / 2 h / 130 °C

2: trichlorophosphate / 2 h / 100 °C

3: potassium carbonate; 1,1'-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex / tetrahydrofuran / 6 h / Reflux

4: N,N-dimethyl-formamide / 16 h / 100 °C

5: 1H-imidazole / N,N-dimethyl-formamide / 2 h

6: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 3 h / Reflux

7: N,N-dimethyl-formamide / 16 h / 60 °C

8: oxone / tetrahydrofuran; water / 16 h / 20 °C

9: hydrazine / ethanol / 0.5 h / 60 °C

10: butan-1-ol / 16 h / 100 °C

11: chiral AD column / Resolution of racemate

With 1H-imidazole; N-Bromosuccinimide; 1,1'-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex; potassium carbonate; hydrazine; trichlorophosphate; dibenzoyl peroxide; In tetrahydrofuran; tetrachloromethane; ethanol; water; N,N-dimethyl-formamide; butan-1-ol;

DOI:10.1016/j.bmcl.2015.01.001

upstream raw materials:

4-amino-6-chloropyrimidine-5-carbonitrile

4-chloro-2-ethyl-6-fluoro-3-phenylquinoline

ethyl 3-(4-fluorophenylamino)-3-oxo-2-phenylpropanoate

3-(4-fluorophenylamino)-3-oxo-2-phenylpropanoic acid

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