2-((2-((R)-3-aminopiperidin-1-yl)-6-(4-fluorophenyl)-4-oxo-4H-pyrrolo[2,3-d]pyrimidin-3(7H)-yl)methyl)benzonitrile

Base Information

• Chemical Name: 2-((2-((R)-3-aminopiperidin-1-yl)-6-(4-fluorophenyl)-4-oxo-4H-pyrrolo[2,3-d]pyrimidin-3(7H)-yl)methyl)benzonitrile
• CAS No.: 1377432-72-8
• Molecular Formula: C₂₅H₂₃FN₆O
• Molecular Weight: 442.496

Synonyms:2-((2-((R)-3-aminopiperidin-1-yl)-6-(4-fluorophenyl)-4-oxo-4H-pyrrolo[2,3-d]pyrimidin-3(7H)-yl)methyl)benzonitrile

Chemical Property of 2-((2-((R)-3-aminopiperidin-1-yl)-6-(4-fluorophenyl)-4-oxo-4H-pyrrolo[2,3-d]pyrimidin-3(7H)-yl)methyl)benzonitrile

Chemical Property:

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Technology Process of 2-((2-((R)-3-aminopiperidin-1-yl)-6-(4-fluorophenyl)-4-oxo-4H-pyrrolo[2,3-d]pyrimidin-3(7H)-yl)methyl)benzonitrile

There total 8 articles about 2-((2-((R)-3-aminopiperidin-1-yl)-6-(4-fluorophenyl)-4-oxo-4H-pyrrolo[2,3-d]pyrimidin-3(7H)-yl)methyl)benzonitrile 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: 41.2%

tert-butyl ((3R)-1-(3-(2-cyanobenzyl)-6-(4-fluorophenyl)-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-2-yl)piperidin-3-yl)carbamate (1377432-88-6) → 2-((2-((R)-3-aminopiperidin-1-yl)-6-(4-fluorophenyl)-4-oxo-4H-pyrrolo[2,3-d]pyrimidin-3(7H)-yl)methyl)benzonitrile (1377432-72-8)

Guidance literature:

tert-butyl ((3R)-1-(3-(2-cyanobenzyl)-6-(4-fluorophenyl)-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-2-yl)piperidin-3-yl)carbamate; With trifluoroacetic acid; In dichloromethane; at 0 - 20 ℃;

With sodium hydrogencarbonate; In dichloromethane; water; pH=7; Cooling with ice;

DOI:10.1016/j.ejmech.2012.03.015

Reference yield:

2-chloro-7H-pyrrolo[2,3-d]pyrimidin-4-ol (1245811-22-6) → 2-((2-((R)-3-aminopiperidin-1-yl)-6-(4-fluorophenyl)-4-oxo-4H-pyrrolo[2,3-d]pyrimidin-3(7H)-yl)methyl)benzonitrile (1377432-72-8)

Guidance literature:

Multi-step reaction with 7 steps

1.1: dmap; triethylamine / tetrahydrofuran / 0.5 h / 0 °C

1.2: 20 °C

2.1: sodium hydride / 1,2-dimethoxyethane; N,N-dimethyl-formamide / 0.33 h / 0 °C

2.2: 0 - 20 °C

2.3: 65 °C

3.1: sodium hydrogencarbonate / ethanol / 6 h / 150 °C

4.1: potassium carbonate / dichloromethane / 0.5 h / 0 °C

4.2: 20 °C

5.1: N-Bromosuccinimide / dichloromethane / 4 h / 20 °C

6.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; tert-butylamine / water; isopropyl alcohol / 100 °C / Inert atmosphere

7.1: trifluoroacetic acid / dichloromethane / 0 - 20 °C

7.2: pH 7 / Cooling with ice

With dmap; N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium hydride; sodium hydrogencarbonate; potassium carbonate; tert-butylamine; triethylamine; trifluoroacetic acid; In tetrahydrofuran; 1,2-dimethoxyethane; ethanol; dichloromethane; water; N,N-dimethyl-formamide; isopropyl alcohol; 6.1: Suzuki coupling;

DOI:10.1016/j.ejmech.2012.03.015

Reference yield:

tert-butyl 2-chloro-4-hydroxy-7H-pyrrolo[2,3-d]pyrimidine-7-carboxylate (1245811-23-7) → 2-((2-((R)-3-aminopiperidin-1-yl)-6-(4-fluorophenyl)-4-oxo-4H-pyrrolo[2,3-d]pyrimidin-3(7H)-yl)methyl)benzonitrile (1377432-72-8)

Guidance literature:

Multi-step reaction with 6 steps

1.1: sodium hydride / 1,2-dimethoxyethane; N,N-dimethyl-formamide / 0.33 h / 0 °C

1.2: 0 - 20 °C

1.3: 65 °C

2.1: sodium hydrogencarbonate / ethanol / 6 h / 150 °C

3.1: potassium carbonate / dichloromethane / 0.5 h / 0 °C

3.2: 20 °C

4.1: N-Bromosuccinimide / dichloromethane / 4 h / 20 °C

5.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; tert-butylamine / water; isopropyl alcohol / 100 °C / Inert atmosphere

6.1: trifluoroacetic acid / dichloromethane / 0 - 20 °C

6.2: pH 7 / Cooling with ice

With N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium hydride; sodium hydrogencarbonate; potassium carbonate; tert-butylamine; trifluoroacetic acid; In 1,2-dimethoxyethane; ethanol; dichloromethane; water; N,N-dimethyl-formamide; isopropyl alcohol; 5.1: Suzuki coupling;

DOI:10.1016/j.ejmech.2012.03.015

upstream raw materials:

2-chloro-7H-pyrrolo[2,3-d]pyrimidin-4-ol

tert-butyl 2-chloro-4-hydroxy-7H-pyrrolo[2,3-d]pyrimidine-7-carboxylate

2-((2-chloro-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-3-yl)methyl)benzonitrile

2-((2-((R)-3-aminopiperidin-1-yl)-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-3-yl)methyl)benzonitrile

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