7-Tosyl-7H-Pyrrolo[2,3-d]pyrimidine-5-boronic acid pinacol ester

Base Information

• Chemical Name: 7-Tosyl-7H-Pyrrolo[2,3-d]pyrimidine-5-boronic acid pinacol ester
• CAS No.: 934178-97-9
• Molecular Formula: C19H24BN3O5S
• Molecular Weight: 399.278
• Hs Code.: 2933990090
• Mol file: 934178-97-9.mol

Synonyms:7-(4-methylbenzenesulfonyl)-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-7H-pyrrolo[2,3-d]pyrimidine; 5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine; 5-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-1H-PYRROLO[2,3-B]PYRIDINE

Chemical Property of 7-Tosyl-7H-Pyrrolo[2,3-d]pyrimidine-5-boronic acid pinacol ester

Chemical Property:

• Boiling Point: 576.6±60.0 °C(Predicted)
• PKA: 2.84±0.30(Predicted)
• PSA: 91.69000
• Density: 1.29±0.1 g/cm3(Predicted)
• LogP: 3.35670
• Storage Temp.: 2-8°C

Purity/Quality:

99%, ^*data from raw suppliers

7-Tosyl-7H-Pyrrolo[2,3-d]pyrimidine-5-boronicacidpinacolester 97.0% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 7-Tosyl-7H-Pyrrolo[2,3-d]pyrimidine-5-boronic acid pinacol ester

There total 4 articles about 7-Tosyl-7H-Pyrrolo[2,3-d]pyrimidine-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: 98.0%

5-bromo-7-(p-toluenesulfonyl)-7H-pyrrolo[2,3-d]pyrimidine (934178-96-8) + bis(pinacol)diborane (73183-34-3) → 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-7-(p-toluenesulfonyl)-7H-pyrrolo[2,3-d]pyrimidine (934178-97-9)

Guidance literature:

With potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,2-dimethoxyethane; at 150 ℃; for 0.166667h; microwave irradiation;

Reference yield:

7H-pyrrolo[2,3-d]pyrimidine (271-70-5) → 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-7-(p-toluenesulfonyl)-7H-pyrrolo[2,3-d]pyrimidine (934178-97-9)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium hydride / tetrahydrofuran / 20 °C

2: bromine / dichloromethane

3: potassium acetate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane; water / 95 °C / Inert atmosphere

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; bromine; potassium acetate; sodium hydride; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; 3: |Suzuki Coupling;

DOI:10.1021/acs.jmedchem.5b00301

Reference yield:

p-toluenesulfonyl chloride (98-59-9) → 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-7-(p-toluenesulfonyl)-7H-pyrrolo[2,3-d]pyrimidine (934178-97-9)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium hydride / tetrahydrofuran / 20 °C

2: bromine / dichloromethane

3: potassium acetate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane; water / 95 °C / Inert atmosphere

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; bromine; potassium acetate; sodium hydride; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; 3: |Suzuki Coupling;

DOI:10.1021/acs.jmedchem.5b00301

upstream raw materials:

5-bromo-7-(p-toluenesulfonyl)-7H-pyrrolo[2,3-d]pyrimidine

bis(pinacol)diborane

7H-pyrrolo[2,3-d]pyrimidine

p-toluenesulfonyl chloride

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