2-AMINO-4-TRIFLUOROPYRIMIDINE-5-BORONIC ACID PINACOL ESTER

Base Information

• Chemical Name: 2-AMINO-4-TRIFLUOROPYRIMIDINE-5-BORONIC ACID PINACOL ESTER
• CAS No.: 944401-58-5
• Molecular Formula: C11H15BF3N3O2
• Molecular Weight: 289.065
• Hs Code.: 2934999090
• Mol file: 944401-58-5.mol

Synonyms:[5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-4-(trifluoromethyl)pyrimidin-2-yl]amine;

Chemical Property of 2-AMINO-4-TRIFLUOROPYRIMIDINE-5-BORONIC ACID PINACOL ESTER

Chemical Property:

• Boiling Point: 403.837 °C at 760 mmHg
• Flash Point: 198.034 °C
• PSA: 70.26000
• Density: 1.28 g/cm³
• LogP: 1.95800
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C

Purity/Quality:

98%,99%, ^*data from raw suppliers

2-Amino-4-trifluoromethylpyrimidine-5-boronic acid pinacol ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-AMINO-4-TRIFLUOROPYRIMIDINE-5-BORONIC ACID PINACOL ESTER

There total 4 articles about 2-AMINO-4-TRIFLUOROPYRIMIDINE-5-BORONIC ACID PINACOL ESTER 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: 42.0%

5-bromo-4-(trifluoromethyl)-2-pyrimidylamine (935534-47-7) + bis(pinacol)diborane (73183-34-3) → 5-(4,4,5,5-tetramethyl(1,3,2-dioxaborolan-2-yl))-4-(trifluoromethyl)pyrimidine-2-ylamine (944401-58-5)

Guidance literature:

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; In 1,4-dioxane; at 115 ℃; for 4h; Inert atmosphere;

Reference yield:

5-bromo-4-(trifluoromethyl)-2-pyrimidylamine (935534-47-7) + bis(pinacol)diborane (73183-34-3) → 5-(4,4,5,5-tetramethyl(1,3,2-dioxaborolan-2-yl))-4-(trifluoromethyl)pyrimidine-2-ylamine (944401-58-5) + 2-amino-4-trifluoromethylpyrimidine (16075-42-6)

Guidance literature:

With potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; at 115 ℃; for 6h;

Reference yield:

2-amino-4-trifluoromethylpyrimidine (16075-42-6) → 5-(4,4,5,5-tetramethyl(1,3,2-dioxaborolan-2-yl))-4-(trifluoromethyl)pyrimidine-2-ylamine (944401-58-5)

Guidance literature:

Multi-step reaction with 2 steps

1: N-Bromosuccinimide / acetonitrile / 4.5 h / 20 °C / Darkness

2: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate / 1,4-dioxane / 4 h / 115 °C / Inert atmosphere

With N-Bromosuccinimide; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; In 1,4-dioxane; acetonitrile;

upstream raw materials:

5-bromo-4-(trifluoromethyl)-2-pyrimidylamine

bis(pinacol)diborane

2-amino-4-trifluoromethylpyrimidine

Downstream raw materials:

(S)-3-(2'-amino-2-(morpholin-4-yl)-4'-trifluoromethyl-[4,5']bipyrimidinyl-6-yl)-4-(((tert-butyldiphenylsilanyl)oxy)methyl)-[1,3]oxazinan-2-one

(S)-3-(2'-amino-2-(morpholin-4-yl)-4'-(trifluoromethyl)-[4,5']bipyrimidinyl-6-yl)-4-(((tertbutyldiphenylsilanyl)oxy)methyl)-5,5-dimethyloxazolidin-2-one

(4S,5S)-3-(2'-amino-2-morpholino-4'-(trifluoromethyl)-[4,5'-bipyrimidin]-6-yl)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-5-(4-methoxyphenyl)oxazolidin-2-one

(4S,5S)-3-(2'-amino-2-morpholino-4'-(trifluoromethyl)-[4,5'-bipyrimidin]-6-yl)-4-(hydroxymethyl)-5-(4-methoxyphenyl)oxazolidin-2-one

Refernces

• 1、 -. "MECHANISTIC TARGET OF RAPAMYCIN SIGNALING PATHWAY INHIBITORS AND THERAPEUTIC APPLICATIONS THEREOF". Paragraph 00218; 00219. . Retrieved 2018/04/11.
• 2、 -. "Oxazolidin-2-one-Pyrimidine Derivatives". Paragraph 0218. . Retrieved 2014/05/20.