6-amino-3-bromo-2-[2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl]-4-isopropoxy-1H-pyrazolo[3,4-d]pyrimidine

Base Information

• Chemical Name: 6-amino-3-bromo-2-[2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl]-4-isopropoxy-1H-pyrazolo[3,4-d]pyrimidine
• CAS No.: 190430-40-1
• Molecular Formula: C₂₉H₃₀BrN₅O₆
• Molecular Weight: 624.491
• Mol file: 190430-40-1.mol

Synonyms:

Chemical Property of 6-amino-3-bromo-2-[2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl]-4-isopropoxy-1H-pyrazolo[3,4-d]pyrimidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-amino-3-bromo-2-[2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl]-4-isopropoxy-1H-pyrazolo[3,4-d]pyrimidine

There total 3 articles about 6-amino-3-bromo-2-[2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl]-4-isopropoxy-1H-pyrazolo[3,4-d]pyrimidine 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: 41.0%

2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride (4330-21-6) + 3-bromo-4-isopropoxy-1H-pyrazolo[3,4-d]pyrimidin-6-amine (183274-50-2) → 6-amino-3-bromo-2-[2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl]-4-isopropoxy-1H-pyrazolo[3,4-d]pyrimidine (190430-40-1) + 6-amino-3-bromo-1-[2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl]-4-isopropoxy-1H-pyrazolo[3,4-d]pyrimidine (190430-38-7)

Guidance literature:

With sodium hydride; In acetonitrile; for 0.5h; Ambient temperature;

DOI:10.1080/07328319708001351

Reference yield:

4-Isopropoxy-1H-pyrazolo[3,4-d]pyrimidin-6-ylamine (183274-49-9) → 6-amino-3-bromo-2-[2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl]-4-isopropoxy-1H-pyrazolo[3,4-d]pyrimidine (190430-40-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 78 percent / NBS / 1,2-dichloro-ethane / 1.5 h / Heating

2: 17 percent / NaH / acetonitrile / 1.) r.t., 10 min, 2.) r.t., 20 min

With N-Bromosuccinimide; sodium hydride; In 1,2-dichloro-ethane; acetonitrile;

DOI:10.1055/s-1998-4483

Reference yield:

4-chloro-1H-pyrazolo[3,4-d]pyrimidine-6-amine (100644-65-3) → 6-amino-3-bromo-2-[2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl]-4-isopropoxy-1H-pyrazolo[3,4-d]pyrimidine (190430-40-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 77 percent / i-PrONa / 1 h / Heating

2: 78 percent / NBS / 1,2-dichloro-ethane / 1.5 h / Heating

3: 17 percent / NaH / acetonitrile / 1.) r.t., 10 min, 2.) r.t., 20 min

With N-Bromosuccinimide; sodium isopropylate; sodium hydride; In 1,2-dichloro-ethane; acetonitrile;

DOI:10.1055/s-1998-4483

upstream raw materials:

2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride

3-bromo-4-isopropoxy-1H-pyrazolo[3,4-d]pyrimidin-6-amine

4-chloro-1H-pyrazolo[3,4-d]pyrimidine-6-amine

4-Isopropoxy-1H-pyrazolo[3,4-d]pyrimidin-6-ylamine

Downstream raw materials:

2-[2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl]-4-isopropoxy-2H-pyrazolo[3,4-d]pyrimidin-6-amine