(5-aminopyridin-3-yl){7-(2-{[tert-butyl(dimethyl)silyl]oxy}-1,1-dimethylethyl)-2-[(2,4-dimethoxybenzyl)amino]-7H-pyrrolo[2,3-d]pyrimidin-5-yl}methanone

Base Information

• Chemical Name: (5-aminopyridin-3-yl){7-(2-{[tert-butyl(dimethyl)silyl]oxy}-1,1-dimethylethyl)-2-[(2,4-dimethoxybenzyl)amino]-7H-pyrrolo[2,3-d]pyrimidin-5-yl}methanone
• CAS No.: 1402445-23-1
• Molecular Formula: C₃₁H₄₂N₆O₄Si
• Molecular Weight: 590.798
• Mol file: 1402445-23-1.mol

Synonyms:

Chemical Property of (5-aminopyridin-3-yl){7-(2-{[tert-butyl(dimethyl)silyl]oxy}-1,1-dimethylethyl)-2-[(2,4-dimethoxybenzyl)amino]-7H-pyrrolo[2,3-d]pyrimidin-5-yl}methanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5-aminopyridin-3-yl){7-(2-{[tert-butyl(dimethyl)silyl]oxy}-1,1-dimethylethyl)-2-[(2,4-dimethoxybenzyl)amino]-7H-pyrrolo[2,3-d]pyrimidin-5-yl}methanone

There total 10 articles about (5-aminopyridin-3-yl){7-(2-{[tert-butyl(dimethyl)silyl]oxy}-1,1-dimethylethyl)-2-[(2,4-dimethoxybenzyl)amino]-7H-pyrrolo[2,3-d]pyrimidin-5-yl}methanone 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:

C44H50N6O4Si → (5-aminopyridin-3-yl){7-(2-{[tert-butyl(dimethyl)silyl]oxy}-1,1-dimethylethyl)-2-[(2,4-dimethoxybenzyl)amino]-7H-pyrrolo[2,3-d]pyrimidin-5-yl}methanone (1402445-23-1)

Guidance literature:

With citric acid; In tetrahydrofuran; water; at 20 ℃; for 5h; Inert atmosphere;

DOI:10.1021/acs.jmedchem.6b00850

Reference yield:

2-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine (1060815-90-8) → (5-aminopyridin-3-yl){7-(2-{[tert-butyl(dimethyl)silyl]oxy}-1,1-dimethylethyl)-2-[(2,4-dimethoxybenzyl)amino]-7H-pyrrolo[2,3-d]pyrimidin-5-yl}methanone (1402445-23-1)

Guidance literature:

Multi-step reaction with 7 steps

1.1: potassium iodide; caesium carbonate / N,N-dimethyl-formamide / 19 h / 60 °C / Inert atmosphere

2.1: lithium hydroxide monohydrate / tetrahydrofuran; water / 3 h / 60 °C / Inert atmosphere

3.1: diisobutylaluminium hydride / tetrahydrofuran / 1.5 h / 0 °C / Inert atmosphere

4.1: 1H-imidazole / N,N-dimethyl-formamide / 16 h / 0 - 20 °C / Inert atmosphere

5.1: isopropylmagnesium chloride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

5.2: 16 h / 0 - 20 °C / Inert atmosphere

6.1: dmap / 1,4-dioxane / 48 h / Inert atmosphere; Reflux

7.1: citric acid / tetrahydrofuran; water / 5 h / 20 °C / Inert atmosphere

With 1H-imidazole; dmap; lithium hydroxide monohydrate; isopropylmagnesium chloride; diisobutylaluminium hydride; caesium carbonate; citric acid; potassium iodide; In tetrahydrofuran; 1,4-dioxane; water; N,N-dimethyl-formamide;

DOI:10.1021/acs.jmedchem.6b00850

Reference yield:

2-chloro-7H-pyrrolo[2,3-d]pyrimidine (335654-06-3) → (5-aminopyridin-3-yl){7-(2-{[tert-butyl(dimethyl)silyl]oxy}-1,1-dimethylethyl)-2-[(2,4-dimethoxybenzyl)amino]-7H-pyrrolo[2,3-d]pyrimidin-5-yl}methanone (1402445-23-1)

Guidance literature:

Multi-step reaction with 8 steps

1.1: N-iodo-succinimide / acetonitrile / 1 h / 12 - 20 °C / Inert atmosphere

2.1: potassium iodide; caesium carbonate / N,N-dimethyl-formamide / 19 h / 60 °C / Inert atmosphere

3.1: lithium hydroxide monohydrate / tetrahydrofuran; water / 3 h / 60 °C / Inert atmosphere

4.1: diisobutylaluminium hydride / tetrahydrofuran / 1.5 h / 0 °C / Inert atmosphere

5.1: 1H-imidazole / N,N-dimethyl-formamide / 16 h / 0 - 20 °C / Inert atmosphere

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

6.2: 16 h / 0 - 20 °C / Inert atmosphere

7.1: dmap / 1,4-dioxane / 48 h / Inert atmosphere; Reflux

8.1: citric acid / tetrahydrofuran; water / 5 h / 20 °C / Inert atmosphere

With 1H-imidazole; dmap; N-iodo-succinimide; lithium hydroxide monohydrate; isopropylmagnesium chloride; diisobutylaluminium hydride; caesium carbonate; citric acid; potassium iodide; In tetrahydrofuran; 1,4-dioxane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/acs.jmedchem.6b00850

upstream raw materials:

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

2-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine

N-methyl-N-methoxy-5-bromopyridine-3-carboxamide

Downstream raw materials:

PF-06273340

Refernces