(5S)-5-amino-7-hydroxy-2-phenyl-2,4,5,7-tetrahydro-6H-pyrazolo[3,4-b]pyridin-6-one

Base Information

• Chemical Name: (5S)-5-amino-7-hydroxy-2-phenyl-2,4,5,7-tetrahydro-6H-pyrazolo[3,4-b]pyridin-6-one
• CAS No.: 1380349-01-8
• Molecular Formula: C₁₂H₁₂N₄O₂
• Molecular Weight: 244.253
• Mol file: 1380349-01-8.mol

Synonyms:

Chemical Property of (5S)-5-amino-7-hydroxy-2-phenyl-2,4,5,7-tetrahydro-6H-pyrazolo[3,4-b]pyridin-6-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5S)-5-amino-7-hydroxy-2-phenyl-2,4,5,7-tetrahydro-6H-pyrazolo[3,4-b]pyridin-6-one

There total 10 articles about (5S)-5-amino-7-hydroxy-2-phenyl-2,4,5,7-tetrahydro-6H-pyrazolo[3,4-b]pyridin-6-one 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:

3-amino-1-phenyl-1H-pyrazole-4-carbonitrile (138942-61-7) → (5S)-5-amino-7-hydroxy-2-phenyl-2,4,5,7-tetrahydro-6H-pyrazolo[3,4-b]pyridin-6-one (1380349-01-8)

Guidance literature:

Multi-step reaction with 10 steps

1: sodium peroxoborate tetrahydrate / trifluoroacetic acid

2: water; lithium hydroxide / methanol

3: dimethylsulfide borane complex / tetrahydrofuran / -20 °C / Reflux

4: carbon tetrabromide; triphenylphosphine / dichloromethane

5: O-allyl-N-(9-anthracenylmethyl)cinchonidinium bromide; cesiumhydroxide monohydrate / dichloromethane / -30 °C

6: trifluoroacetic acid / dichloromethane

7: sodium hydroxide / tetrahydrofuran

8: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane

9: platinum on carbon; hydrogen / pyridine / 1551.49 Torr

10: hydrogenchloride / 1,4-dioxane

With hydrogenchloride; dmap; cesiumhydroxide monohydrate; sodium peroxoborate tetrahydrate; carbon tetrabromide; dimethylsulfide borane complex; platinum on carbon; O-allyl-N-(9-anthracenylmethyl)cinchonidinium bromide; water; hydrogen; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triphenylphosphine; trifluoroacetic acid; sodium hydroxide; lithium hydroxide; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; dichloromethane; trifluoroacetic acid;

DOI:10.1016/j.bmcl.2013.02.039

Reference yield:

C10H9N3O3 → (5S)-5-amino-7-hydroxy-2-phenyl-2,4,5,7-tetrahydro-6H-pyrazolo[3,4-b]pyridin-6-one (1380349-01-8)

Guidance literature:

Multi-step reaction with 7 steps

1: carbon tetrabromide; triphenylphosphine / dichloromethane

2: O-allyl-N-(9-anthracenylmethyl)cinchonidinium bromide; cesiumhydroxide monohydrate / dichloromethane / -30 °C

3: trifluoroacetic acid / dichloromethane

4: sodium hydroxide / tetrahydrofuran

5: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane

6: platinum on carbon; hydrogen / pyridine / 1551.49 Torr

7: hydrogenchloride / 1,4-dioxane

With hydrogenchloride; dmap; cesiumhydroxide monohydrate; carbon tetrabromide; platinum on carbon; O-allyl-N-(9-anthracenylmethyl)cinchonidinium bromide; hydrogen; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triphenylphosphine; trifluoroacetic acid; sodium hydroxide; In tetrahydrofuran; 1,4-dioxane; pyridine; dichloromethane;

DOI:10.1016/j.bmcl.2013.02.039

Reference yield:

C10H8BrN3O2 → (5S)-5-amino-7-hydroxy-2-phenyl-2,4,5,7-tetrahydro-6H-pyrazolo[3,4-b]pyridin-6-one (1380349-01-8)

Guidance literature:

Multi-step reaction with 6 steps

1: O-allyl-N-(9-anthracenylmethyl)cinchonidinium bromide; cesiumhydroxide monohydrate / dichloromethane / -30 °C

2: trifluoroacetic acid / dichloromethane

3: sodium hydroxide / tetrahydrofuran

4: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane

5: platinum on carbon; hydrogen / pyridine / 1551.49 Torr

6: hydrogenchloride / 1,4-dioxane

With hydrogenchloride; dmap; cesiumhydroxide monohydrate; platinum on carbon; O-allyl-N-(9-anthracenylmethyl)cinchonidinium bromide; hydrogen; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; sodium hydroxide; In tetrahydrofuran; 1,4-dioxane; pyridine; dichloromethane;

DOI:10.1016/j.bmcl.2013.02.039

upstream raw materials:

3-amino-1-phenyl-1H-pyrazole-4-carbonitrile

C₁₀H₇N₃O₄

Refernces