Technology Process of methyl {4,6-diamino-2-[5-fluoro-1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]pyrimidin-5-yl}methylcarbamate
There total 13 articles about methyl {4,6-diamino-2-[5-fluoro-1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]pyrimidin-5-yl}methylcarbamate which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
methyl {4,6-diamino-2-[5-fluoro-1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine-3-yl]pyrimidin-5-yl}carbamate;
With
lithium hexamethyldisilazane;
In
tetrahydrofuran;
at 0 ℃;
for 0.333333h;
methyl iodide;
In
tetrahydrofuran;
at 0 - 20 ℃;
for 1h;
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: boron trifluoride diethyl etherate / tetrahydrofuran / 0 °C
1.2: 0.5 h / -10 °C
1.3: 0 - 20 °C
2.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 20 °C
3.1: bis(tri-n-butyltin) / tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane / Inert atmosphere; Reflux
4.1: hydrogen; pyridine / palladium 10% on activated carbon / 20 °C
5.1: pyridine / dichloromethane / 1 h / 0 °C / Inert atmosphere
6.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.33 h / 0 °C
6.2: 1 h / 0 - 20 °C
With
pyridine; boron trifluoride diethyl etherate; hydrogen; bis(tri-n-butyltin); caesium carbonate; lithium hexamethyldisilazane;
tetrakis(triphenylphosphine) palladium(0); palladium 10% on activated carbon;
In
tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide;
- Guidance literature:
-
Multi-step reaction with 9 steps
1.1: zinc; acetic acid / methanol / 24 h / Reflux
2.1: triethylamine; trifluoroacetic anhydride / dichloromethane / 1.5 h / 0 °C
3.1: hydrazine hydrate / ethylene glycol / 4 h / Reflux
4.1: boron trifluoride diethyl etherate / tetrahydrofuran / 0 °C
4.2: 0.5 h / -10 °C
4.3: 0 - 20 °C
5.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 20 °C
6.1: bis(tri-n-butyltin) / tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane / Inert atmosphere; Reflux
7.1: hydrogen; pyridine / palladium 10% on activated carbon / 20 °C
8.1: pyridine / dichloromethane / 1 h / 0 °C / Inert atmosphere
9.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.33 h / 0 °C
9.2: 1 h / 0 - 20 °C
With
pyridine; boron trifluoride diethyl etherate; hydrogen; bis(tri-n-butyltin); caesium carbonate; hydrazine hydrate; acetic acid; triethylamine; trifluoroacetic anhydride; lithium hexamethyldisilazane; zinc;
tetrakis(triphenylphosphine) palladium(0); palladium 10% on activated carbon;
In
tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; ethylene glycol; N,N-dimethyl-formamide;