5-{1-[4-amino-3-(difluoromethyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]ethyl}-3-[1-(2-hydroxyethyl)azetidin-3-yl]-4-methoxy-2-methylbenzonitrile

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Chemical Name:5-{1-[4-amino-3-(difluoromethyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]ethyl}-3-[1-(2-hydroxyethyl)azetidin-3-yl]-4-methoxy-2-methylbenzonitrile
CAS No.:1426696-66-3
Molecular Formula:C₂₂H₂₅F₂N₇O₂
Molecular Weight:457.483
Hs Code.:

Synonyms:5-{1-[4-amino-3-(difluoromethyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]ethyl}-3-[1-(2-hydroxyethyl)azetidin-3-yl]-4-methoxy-2-methylbenzonitrile

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Chemical Property of 5-{1-[4-amino-3-(difluoromethyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]ethyl}-3-[1-(2-hydroxyethyl)azetidin-3-yl]-4-methoxy-2-methylbenzonitrile

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Technology Process of 5-{1-[4-amino-3-(difluoromethyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]ethyl}-3-[1-(2-hydroxyethyl)azetidin-3-yl]-4-methoxy-2-methylbenzonitrile

There total 16 articles about 5-{1-[4-amino-3-(difluoromethyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]ethyl}-3-[1-(2-hydroxyethyl)azetidin-3-yl]-4-methoxy-2-methylbenzonitrile 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:

: C₂₈H₃₉F₂N₇O₂Si

: 1426696-66-3
5-{1-[4-amino-3-(difluoromethyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]ethyl}-3-[1-(2-hydroxyethyl)azetidin-3-yl]-4-methoxy-2-methylbenzonitrile

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 1.5h;

Reference yield:

: 1382996-71-5
tert-butyl 3-(3-acetyl-5-chloro-2-methoxy-6-methylphenyl)azetidine-1-carboxylate

: 1426696-66-3
5-{1-[4-amino-3-(difluoromethyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]ethyl}-3-[1-(2-hydroxyethyl)azetidin-3-yl]-4-methoxy-2-methylbenzonitrile

Guidance literature:: Multi-step reaction with 13 steps

1: sodium tetrahydroborate; methanol / 1 h / 0 - 5 °C

2: 1,3,5-trichloro-2,4,6-triazine; N,N-dimethyl-formamide / dichloromethane / 20 °C

3: caesium carbonate; potassium iodide / N,N-dimethyl-formamide / 4 h / 120 °C

4: trifluoroacetic acid / dichloromethane / 2 h / 20 °C

5: triethylamine / acetonitrile / 20 °C

6: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / N,N-dimethyl-formamide; water / 3 h / 100 °C / Inert atmosphere

7: osmium(VIII) oxide; 4-methylmorpholine N-oxide; water / tert-butyl alcohol / 20 °C

8: sodium periodate; acetic acid / water; tetrahydrofuran / 3 h / 0 °C

9: diethylamino-sulfur trifluoride / dichloromethane / 2.5 h / 0 - 20 °C

10: zinc; bis(tri-t-butylphosphine)palladium⁽⁰⁾ / 1-methyl-pyrrolidin-2-one / 3 h / 130 °C / Inert atmosphere

11: hydrogenchloride / dichloromethane; 1,4-dioxane / 3.5 h / 20 °C

12: triethylamine / dichloromethane / 3 h / 20 °C

13: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 20 °C

With hydrogenchloride; methanol; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 1,3,5-trichloro-2,4,6-triazine; bis(tri-t-butylphosphine)palladium⁽⁰⁾; diethylamino-sulfur trifluoride; tetrabutyl ammonium fluoride; water; sodium carbonate; caesium carbonate; acetic acid; 4-methylmorpholine N-oxide; triethylamine; N,N-dimethyl-formamide; trifluoroacetic acid; potassium iodide; zinc; In tetrahydrofuran; 1,4-dioxane; 1-methyl-pyrrolidin-2-one; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol;

Reference yield:

: 1426699-08-2
tert-butyl 3-[3-chloro-5-(1-chloroethyl)-6-methoxy-2-methylphenyl]azetidine-1-carboxylate

: 1426696-66-3
5-{1-[4-amino-3-(difluoromethyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]ethyl}-3-[1-(2-hydroxyethyl)azetidin-3-yl]-4-methoxy-2-methylbenzonitrile

Guidance literature:: Multi-step reaction with 11 steps

1: caesium carbonate; potassium iodide / N,N-dimethyl-formamide / 4 h / 120 °C

2: trifluoroacetic acid / dichloromethane / 2 h / 20 °C

3: triethylamine / acetonitrile / 20 °C

4: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / N,N-dimethyl-formamide; water / 3 h / 100 °C / Inert atmosphere

5: osmium(VIII) oxide; 4-methylmorpholine N-oxide; water / tert-butyl alcohol / 20 °C

6: sodium periodate; acetic acid / water; tetrahydrofuran / 3 h / 0 °C

7: diethylamino-sulfur trifluoride / dichloromethane / 2.5 h / 0 - 20 °C

8: zinc; bis(tri-t-butylphosphine)palladium⁽⁰⁾ / 1-methyl-pyrrolidin-2-one / 3 h / 130 °C / Inert atmosphere

9: hydrogenchloride / dichloromethane; 1,4-dioxane / 3.5 h / 20 °C

10: triethylamine / dichloromethane / 3 h / 20 °C

11: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 20 °C

With hydrogenchloride; sodium periodate; osmium(VIII) oxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; bis(tri-t-butylphosphine)palladium⁽⁰⁾; diethylamino-sulfur trifluoride; tetrabutyl ammonium fluoride; water; sodium carbonate; caesium carbonate; acetic acid; 4-methylmorpholine N-oxide; triethylamine; trifluoroacetic acid; potassium iodide; zinc; In tetrahydrofuran; 1,4-dioxane; 1-methyl-pyrrolidin-2-one; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol;