3-(4-Phenoxy-phenyl)-1-piperidin-3-yl-1H-pyrazolo[3,4-d]pyriMidin-4-ylaMine

Base Information

• Chemical Name: 3-(4-Phenoxy-phenyl)-1-piperidin-3-yl-1H-pyrazolo[3,4-d]pyriMidin-4-ylaMine
• CAS No.: 1022150-12-4
• Molecular Formula: C22H22N6O
• Molecular Weight: 386.456
• Mol file: 1022150-12-4.mol

Synonyms:3-(4-Phenoxy-phenyl)-1-piperidin-3-yl-1H-pyrazolo[3,4-d]pyriMidin-4-ylaMine;(R)-3-(4-phenoxyphenyl)-1-(piperidin-3-yl)-1H-pyrazolo[3,4-d]pyriMidin-4-aMine;3-(4-Phenoxy-phenyl)-1-(R)-piperidin-3-yl-1H-pyrazolo[3,4-d]pyriMidin-4-ylaMine;Btk inhibitor 1 (R enantioMer);ibrutinib N-1;3-(4-phenoxyphenyl)-1-(3-piperidyl)pyrazolo[3,4-d]pyriMidin-4-aMine;Ibrutinib intermeidate N-1;3-(4-Phenoxyphenyl)-1-(piperidin-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Chemical Property of 3-(4-Phenoxy-phenyl)-1-piperidin-3-yl-1H-pyrazolo[3,4-d]pyriMidin-4-ylaMine

Chemical Property:

• Boiling Point: 626.3±55.0 °C(Predicted)
• PKA: 9.00±0.10(Predicted)
• PSA: 90.88000
• Density: 1.39±0.1 g/cm3(Predicted)
• LogP: 4.70230
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility.: DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

98% ^*data from raw suppliers

(R)-3-(4-Phenoxyphenyl)-1-(piperidin-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: IBT6A is a Btk kinase inhibitor. This compound is a precurser for the manufacture of ibrutinib.
• Uses: (R)-3-(4-Phenoxyphenyl)-1-(piperidin-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine is an intermediate used to prepare pyrazolo-pyrimidine compounds as inhibitors of Bruton''s tyrosine kinase. It is also an intermediate for Ibrutinib (I124970) derivatives.

Technology Process of 3-(4-Phenoxy-phenyl)-1-piperidin-3-yl-1H-pyrazolo[3,4-d]pyriMidin-4-ylaMine

There total 60 articles about 3-(4-Phenoxy-phenyl)-1-piperidin-3-yl-1H-pyrazolo[3,4-d]pyriMidin-4-ylaMine 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: 99.0%

(3R)-3-[4-(benzyloxycarbonylamino)-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carboxylic acid benzyl ester → (R)-3-(4-phenoxyphenyl)-1-(piperidine-3-yl)-1H-pyrazolo[3,4-d]pyrimidine-4-amine (1022150-12-4)

Guidance literature:

With palladium on activated charcoal;

Reference yield: 92.1%

tert-butyl (3R)-3-(4-amino-3-bromo-1H-pyrazolo [3,4-d]pyrimidin-1-yl)piperidine-1-carboxylate (1419223-01-0) + 4-phenoxyphenylboronic acid (51067-38-0) → (R)-3-(4-phenoxyphenyl)-1-(piperidine-3-yl)-1H-pyrazolo[3,4-d]pyrimidine-4-amine (1022150-12-4)

Guidance literature:

tert-butyl (3R)-3-(4-amino-3-bromo-1H-pyrazolo [3,4-d]pyrimidin-1-yl)piperidine-1-carboxylate; 4-phenoxyphenylboronic acid; With potassium phosphate; In 1,4-dioxane; water; for 0.333333h; Inert atmosphere;

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,4-dioxane; water; for 3.08333h; Inert atmosphere; Reflux;

Reference yield: 90.0%

4-phenoxyphenylboronic acid (51067-38-0) + C10H13BrN6*2ClH → (R)-3-(4-phenoxyphenyl)-1-(piperidine-3-yl)-1H-pyrazolo[3,4-d]pyrimidine-4-amine (1022150-12-4)

Guidance literature:

With potassium phosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,4-dioxane; water; for 5h; Solvent; Reagent/catalyst; Inert atmosphere; Reflux;

upstream raw materials:

(3R)‐4‐amino‐3‐(4-phenoxyphenyl)‐1‐(1‐tert-butoxycarbonylpiperidine-3-yl)-1H-pyrazolo[3,4-d]pyrimidine

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

4-Aminopyrazolo<3,4-d>pyrimidin

(R)-3-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carboxylic acid tert-butyl ester

Downstream raw materials:

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

_{(R)-2-(3-(4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carbonyl)-4,4-dimethylpent-2-enenitrile}

ibrutinib

(R,E)-1-(3-(4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]-pyrimidin-1-yl)piperidin-1-yl)-4-(4-(2-aminoethyl)piperazin-1-yl)but-2-en-1-one

Refernces

• 1、 -. "Preparation method of ibrutinib intermediate". . . Retrieved 2021/08/06.
• 2、 -. "Preparation method of precursor of ibrutinib". . . Retrieved 2020/04/22.