(R)-2-(2-((4-amino-3-(2-fluoro-4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)pyrrolidine-1-carbonyi)-3-(1-aminocyciopropyl)acrylonitrile

Base Information

Chemical Name:(R)-2-(2-((4-amino-3-(2-fluoro-4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)pyrrolidine-1-carbonyi)-3-(1-aminocyciopropyl)acrylonitrile
CAS No.:1414354-24-7
Molecular Formula:C₂₉H₂₇FN₈O₂
Molecular Weight:538.584
Hs Code.:

(R)-2-(2-((4-amino-3-(2-fluoro-4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)pyrrolidine-1-carbonyi)-3-(1-aminocyciopropyl)acrylonitrile

Synonyms:(R)-2-(2-((4-amino-3-(2-fluoro-4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)pyrrolidine-1-carbonyi)-3-(1-aminocyciopropyl)acrylonitrile

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Chemical Property of (R)-2-(2-((4-amino-3-(2-fluoro-4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)pyrrolidine-1-carbonyi)-3-(1-aminocyciopropyl)acrylonitrile

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Technology Process of (R)-2-(2-((4-amino-3-(2-fluoro-4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)pyrrolidine-1-carbonyi)-3-(1-aminocyciopropyl)acrylonitrile

There total 11 articles about (R)-2-(2-((4-amino-3-(2-fluoro-4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)pyrrolidine-1-carbonyi)-3-(1-aminocyciopropyl)acrylonitrile 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: 12.0%

: 1414358-09-0
tert-butyl N-[1-[3-[(2R)-2-[[4-amino-3-(2-fluoro-4-phenoxy-phenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]pyrrolidin-1-yl]-2-cyano-3-oxo-prop-1-enyl]cyclopropyl]carbamate

: 1414354-24-7
(R)-2-(2-((4-amino-3-(2-fluoro-4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)pyrrolidine-1-carbonyi)-3-(1-aminocyciopropyl)acrylonitrile

Guidance literature:: With trifluoroacetic acid; In dichloromethane; for 5h;

Reference yield:

: 151266-23-8
4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidine

: 1414354-24-7
(R)-2-(2-((4-amino-3-(2-fluoro-4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)pyrrolidine-1-carbonyi)-3-(1-aminocyciopropyl)acrylonitrile

Guidance literature:: Multi-step reaction with 6 steps

1: triphenylphosphine; di-isopropyl azodicarboxylate / N,N-dimethyl-formamide / 12.5 h / 25 °C / Inert atmosphere

2: sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane; water / 12 h / 80 °C / Inert atmosphere

3: trifluoroacetic acid / dichloromethane / 3 h / 25 °C

4: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 3 h / 25 °C

5: piperidine / dichloromethane; methanol / 6 h / Reflux

6: trifluoroacetic acid / dichloromethane / 5 h

With piperidine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; di-isopropyl azodicarboxylate; sodium carbonate; triethylamine; triphenylphosphine; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide; 1: |Mitsunobu Displacement / 2: |Suzuki Coupling;

Reference yield:

: 121219-03-2
4-bromo-3-fluorophenol

: 1414354-24-7
(R)-2-(2-((4-amino-3-(2-fluoro-4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)pyrrolidine-1-carbonyi)-3-(1-aminocyciopropyl)acrylonitrile

Guidance literature:: Multi-step reaction with 7 steps

1.1: triethylamine; copper diacetate / dichloromethane / 20 °C / Molecular sieve

2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -80 - -70 °C / Inert atmosphere

2.2: 2 h / -80 - -70 °C / Inert atmosphere

3.1: sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane; water / 12 h / 80 °C / Inert atmosphere

4.1: trifluoroacetic acid / dichloromethane / 3 h / 25 °C

5.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 3 h / 25 °C

6.1: piperidine / dichloromethane; methanol / 6 h / Reflux

7.1: trifluoroacetic acid / dichloromethane / 5 h

With piperidine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; copper diacetate; sodium carbonate; triethylamine; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide; 1.1: |Suzuki Coupling / 3.1: |Suzuki Coupling;