tert-butyl (3R)-3-[4-amino-3-[4-(3-fluorophenoxy)phenyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carboxylate

Base Information

• Chemical Name: tert-butyl (3R)-3-[4-amino-3-[4-(3-fluorophenoxy)phenyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carboxylate
• CAS No.: 1414356-50-5
• Molecular Formula: C₂₇H₂₉FN₆O₃
• Molecular Weight: 504.564
• Mol file: 1414356-50-5.mol

Synonyms:tert-butyl (3R)-3-[4-amino-3-[4-(3-fluorophenoxy)phenyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carboxylate

Chemical Property of tert-butyl (3R)-3-[4-amino-3-[4-(3-fluorophenoxy)phenyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (3R)-3-[4-amino-3-[4-(3-fluorophenoxy)phenyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carboxylate

There total 8 articles about tert-butyl (3R)-3-[4-amino-3-[4-(3-fluorophenoxy)phenyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carboxylate 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: 76.0%

(R)-3-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carboxylic acid tert-butyl ester (1276110-38-3) + 2-(4-(3-fluorophenoxy)phenyl )-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1414356-22-1) → tert-butyl (3R)-3-[4-amino-3-[4-(3-fluorophenoxy)phenyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carboxylate (1414356-50-5)

Guidance literature:

With sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,2-dimethoxyethane; water; at 80 ℃; Inert atmosphere;

Reference yield:

4-Aminopyrazolo<3,4-d>pyrimidin (2380-63-4) → tert-butyl (3R)-3-[4-amino-3-[4-(3-fluorophenoxy)phenyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carboxylate (1414356-50-5)

Guidance literature:

Multi-step reaction with 3 steps

1: N-iodo-succinimide / N,N-dimethyl-formamide / 5 h / 80 °C

2: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 12.5 h / 10 - 20 °C

3: sodium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,2-dimethoxyethane; water / 80 °C / Inert atmosphere

With N-iodo-succinimide; di-isopropyl azodicarboxylate; sodium carbonate; triphenylphosphine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,2-dimethoxyethane; water; N,N-dimethyl-formamide;

Reference yield:

4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidine (151266-23-8) → tert-butyl (3R)-3-[4-amino-3-[4-(3-fluorophenoxy)phenyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carboxylate (1414356-50-5)

Guidance literature:

Multi-step reaction with 2 steps

1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 12.5 h / 10 - 20 °C

2: sodium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,2-dimethoxyethane; water / 80 °C / Inert atmosphere

With di-isopropyl azodicarboxylate; sodium carbonate; triphenylphosphine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,2-dimethoxyethane; water;

upstream raw materials:

3-fluorophenylboronic acid

4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidine

4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

4-Aminopyrazolo<3,4-d>pyrimidin

Downstream raw materials:

3-[4-(3-fluorophenoxy)phenyl]-1-[(3R)-piperidin-3-yl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine

(R)-2-(3-(4-amino-3-(4-(3-fluorophenoxy)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carbonyl)-3-cyclopropylacrylonitrile

3-[(3R)-3-[4-amino-3-[4-(3-fluorophenoxy)phenyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidin-1-yl]-3-oxopropanenitrile