methyl {4,6-diamino-2-[5-fluoro-1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]pyrimidin-5-yl}carbamate ethane-1,2-disulphonate

Base Information

• Chemical Name: methyl {4,6-diamino-2-[5-fluoro-1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]pyrimidin-5-yl}carbamate ethane-1,2-disulphonate
• CAS No.: 1350659-00-5
• Molecular Formula: C₂H₆O₆S₂*C₁₉H₁₆F₂N₈O₂
• Molecular Weight: 616.583
• Mol file: 1350659-00-5.mol

Synonyms:methyl {4,6-diamino-2-[5-fluoro-1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]pyrimidin-5-yl}carbamate ethane-1,2-disulphonate

Chemical Property of methyl {4,6-diamino-2-[5-fluoro-1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]pyrimidin-5-yl}carbamate ethane-1,2-disulphonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl {4,6-diamino-2-[5-fluoro-1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]pyrimidin-5-yl}carbamate ethane-1,2-disulphonate

There total 11 articles about methyl {4,6-diamino-2-[5-fluoro-1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]pyrimidin-5-yl}carbamate ethane-1,2-disulphonate 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: 73.7%

ethane-1,2-disulphonic acid (110-04-3) + methyl {4,6-diamino-2-[5-fluoro-1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine-3-yl]pyrimidin-5-yl}carbamate (1350653-20-1) → methyl {4,6-diamino-2-[5-fluoro-1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]pyrimidin-5-yl}carbamate ethane-1,2-disulphonate (1350659-00-5)

Guidance literature:

In 1,4-dioxane; isopropyl alcohol; at 20 ℃;

Reference yield:

2,6-dichloro-5-fluoro-pyridine-3-carbonitrile (82671-02-1) → methyl {4,6-diamino-2-[5-fluoro-1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]pyrimidin-5-yl}carbamate ethane-1,2-disulphonate (1350659-00-5)

Guidance literature:

Multi-step reaction with 10 steps

1.1: sulfuric acid / 1 h / 60 - 65 °C

2.1: zinc; acetic acid / methanol / 24 h / Reflux

3.1: triethylamine; trifluoroacetic anhydride / dichloromethane / 1.5 h / 0 °C

4.1: hydrazine hydrate / ethylene glycol / 4 h / Reflux

5.1: boron trifluoride diethyl etherate; isopentyl nitrite / tetrahydrofuran / -10 - 0 °C

5.2: 0.5 h / 20 °C

6.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 20 °C

7.1: bis(tri-n-butyltin) / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane / Inert atmosphere; Reflux

8.1: hydrogen; pyridine / palladium 10% on activated carbon / 20 °C

9.1: pyridine / dichloromethane / 1 h / 0 °C / Inert atmosphere

10.1: isopropyl alcohol; 1,4-dioxane / 20 °C

With pyridine; sulfuric acid; boron trifluoride diethyl etherate; hydrogen; bis(tri-n-butyltin); caesium carbonate; hydrazine hydrate; acetic acid; triethylamine; trifluoroacetic anhydride; zinc; isopentyl nitrite; tetrakis(triphenylphosphine) palladium⁽⁰⁾; palladium 10% on activated carbon; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; ethylene glycol; N,N-dimethyl-formamide; isopropyl alcohol;

Reference yield:

2,6-dichloro-5-fluoropyridine-3-carboxamide (113237-20-0) → methyl {4,6-diamino-2-[5-fluoro-1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]pyrimidin-5-yl}carbamate ethane-1,2-disulphonate (1350659-00-5)

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; isopentyl nitrite / tetrahydrofuran / -10 - 0 °C

4.2: 0.5 h / 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: isopropyl alcohol; 1,4-dioxane / 20 °C

With pyridine; boron trifluoride diethyl etherate; hydrogen; bis(tri-n-butyltin); caesium carbonate; hydrazine hydrate; acetic acid; triethylamine; trifluoroacetic anhydride; zinc; isopentyl nitrite; tetrakis(triphenylphosphine) palladium⁽⁰⁾; palladium 10% on activated carbon; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; ethylene glycol; N,N-dimethyl-formamide; isopropyl alcohol;

upstream raw materials:

2,6-dichloro-5-fluoropyridine-3-carboxamide

2,6-dichloro-5-fluoro-pyridine-3-carbonitrile

2-chloro-5-fluoropyridine-3-carboxamide

2-chloro-5-fluoronicotinonitrile

Refernces