(R)-N⁴-(5-cyclopropyl-1H-pyrazol-3-yl)-N²-(1-(6-fluoro-1-tosyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)pyrimidine-2,4-diamine

Base Information

• Chemical Name: (R)-N⁴-(5-cyclopropyl-1H-pyrazol-3-yl)-N²-(1-(6-fluoro-1-tosyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)pyrimidine-2,4-diamine
• CAS No.: 1445856-77-8
• Molecular Formula: C₂₆H₂₅FN₈O₂S
• Molecular Weight: 532.601

Synonyms:(R)-N⁴-(5-cyclopropyl-1H-pyrazol-3-yl)-N²-(1-(6-fluoro-1-tosyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)pyrimidine-2,4-diamine

Chemical Property of (R)-N⁴-(5-cyclopropyl-1H-pyrazol-3-yl)-N²-(1-(6-fluoro-1-tosyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)pyrimidine-2,4-diamine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-N⁴-(5-cyclopropyl-1H-pyrazol-3-yl)-N²-(1-(6-fluoro-1-tosyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)pyrimidine-2,4-diamine

There total 11 articles about (R)-N⁴-(5-cyclopropyl-1H-pyrazol-3-yl)-N²-(1-(6-fluoro-1-tosyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)pyrimidine-2,4-diamine 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:

3-amino-2-bromo-5-fluoropyridine (884495-03-8) → (S)-N4-(5-cyclopropyl-1H-pyrazol-3-yl)-N2-(1-(6-fluoro-1-tosyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)pyrimidine-2,4-diamine (1445856-76-7) + (R)-N4-(5-cyclopropyl-1H-pyrazol-3-yl)-N2-(1-(6-fluoro-1-tosyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)pyrimidine-2,4-diamine (1445856-77-8)

Guidance literature:

Multi-step reaction with 10 steps

1.1: triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 2 h / 0 - 20 °C / Inert atmosphere

3.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 - 20 °C

3.2: 0 - 20 °C

4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 20 °C

5.1: N,N-Dimethylcarbamoyl chloride / 1,2-dichloro-ethane / 80 °C / Inert atmosphere

6.1: tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

6.2: Inert atmosphere

7.1: hydroxylamine hydrochloride; sodium acetate / ethanol / 1 h / 60 °C

8.1: zinc; ammonium chloride; acetic acid / methanol / 2 h / 60 °C

9.1: N-ethyl-N,N-diisopropylamine / 15 h / 135 °C

10.1: Resolution of racemate

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; hydroxylamine hydrochloride; sodium acetate; sodium hydride; ammonium chloride; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; N,N-Dimethylcarbamoyl chloride; zinc; In tetrahydrofuran; methanol; ethanol; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; mineral oil;

Reference yield:

N4-(5-cyclopropyl-1H-pyrazol-3-yl)-N2-(1-(6-fluoro-1-tosyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)pyrimidine-2,4-diamine (1445856-75-6) → (S)-N4-(5-cyclopropyl-1H-pyrazol-3-yl)-N2-(1-(6-fluoro-1-tosyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)pyrimidine-2,4-diamine (1445856-76-7) + (R)-N4-(5-cyclopropyl-1H-pyrazol-3-yl)-N2-(1-(6-fluoro-1-tosyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)pyrimidine-2,4-diamine (1445856-77-8)

Guidance literature:

Resolution of racemate;

Reference yield:

6-fluoro-1H-pyrrolo[3,2-b]pyridine (1190320-33-2) → (S)-N4-(5-cyclopropyl-1H-pyrazol-3-yl)-N2-(1-(6-fluoro-1-tosyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)pyrimidine-2,4-diamine (1445856-76-7) + (R)-N4-(5-cyclopropyl-1H-pyrazol-3-yl)-N2-(1-(6-fluoro-1-tosyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)pyrimidine-2,4-diamine (1445856-77-8)

Guidance literature:

Multi-step reaction with 8 steps

1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 - 20 °C

1.2: 0 - 20 °C

2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 20 °C

3.1: N,N-Dimethylcarbamoyl chloride / 1,2-dichloro-ethane / 80 °C / Inert atmosphere

4.1: tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

4.2: Inert atmosphere

5.1: hydroxylamine hydrochloride; sodium acetate / ethanol / 1 h / 60 °C

6.1: zinc; ammonium chloride; acetic acid / methanol / 2 h / 60 °C

7.1: N-ethyl-N,N-diisopropylamine / 15 h / 135 °C

8.1: Resolution of racemate

With hydroxylamine hydrochloride; sodium acetate; sodium hydride; ammonium chloride; acetic acid; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; N,N-Dimethylcarbamoyl chloride; zinc; In tetrahydrofuran; methanol; ethanol; dichloromethane; 1,2-dichloro-ethane; mineral oil;

upstream raw materials:

3-amino-2-bromo-5-fluoropyridine

5-fluoro-2-((trimethylsilyl)ethynyl)pyridin-3-amine

6-fluoro-1H-pyrrolo[3,2-b]pyridine

6-fluoro-1-tosyl-1H-pyrrolo[3,2-b]pyridine

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