N-(5-(hydroxymethyl)-2-methylphenyl)-4-((4-(4-(trifluoromethoxy)phenyl)-5H-pyrrolo[3,2-d]pyrimidin-2-yl)amino)benzamide

Base Information

• Chemical Name: N-(5-(hydroxymethyl)-2-methylphenyl)-4-((4-(4-(trifluoromethoxy)phenyl)-5H-pyrrolo[3,2-d]pyrimidin-2-yl)amino)benzamide
• CAS No.: 1620147-27-4
• Molecular Formula: C₂₈H₂₂F₃N₅O₃
• Molecular Weight: 533.51

Synonyms:N-(5-(hydroxymethyl)-2-methylphenyl)-4-((4-(4-(trifluoromethoxy)phenyl)-5H-pyrrolo[3,2-d]pyrimidin-2-yl)amino)benzamide

Chemical Property of N-(5-(hydroxymethyl)-2-methylphenyl)-4-((4-(4-(trifluoromethoxy)phenyl)-5H-pyrrolo[3,2-d]pyrimidin-2-yl)amino)benzamide

Chemical Property:

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Technology Process of N-(5-(hydroxymethyl)-2-methylphenyl)-4-((4-(4-(trifluoromethoxy)phenyl)-5H-pyrrolo[3,2-d]pyrimidin-2-yl)amino)benzamide

There total 7 articles about N-(5-(hydroxymethyl)-2-methylphenyl)-4-((4-(4-(trifluoromethoxy)phenyl)-5H-pyrrolo[3,2-d]pyrimidin-2-yl)amino)benzamide 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: 38.0%

4-((4-(4-(trifluoromethoxy)phenyl)-5H-pyrrolo[3,2-d]pyrimidin-2-yl)amino)benzoic acid (1620147-26-3) + 3-(hydroxymethyl)-6-methylaniline (81863-45-8) → N-(5-(hydroxymethyl)-2-methylphenyl)-4-((4-(4-(trifluoromethoxy)phenyl)-5H-pyrrolo[3,2-d]pyrimidin-2-yl)amino)benzamide (1620147-27-4)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 80 ℃; for 5h;

DOI:10.1016/j.bmcl.2014.05.066

Reference yield:

methyl 4-((4-(4-(trifluoromethoxy)phenyl)-5H-pyrrolo[3,2-d]pyrimidin-2-yl)amino)benzoate (1620147-25-2) → N-(5-(hydroxymethyl)-2-methylphenyl)-4-((4-(4-(trifluoromethoxy)phenyl)-5H-pyrrolo[3,2-d]pyrimidin-2-yl)amino)benzamide (1620147-27-4)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydroxide; water / methanol / Reflux

2: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 5 h / 80 °C

With water; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; sodium hydroxide; In methanol; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2014.05.066

Reference yield:

4-methoxycarbonyl aniline (619-45-4) → N-(5-(hydroxymethyl)-2-methylphenyl)-4-((4-(4-(trifluoromethoxy)phenyl)-5H-pyrrolo[3,2-d]pyrimidin-2-yl)amino)benzamide (1620147-27-4)

Guidance literature:

Multi-step reaction with 3 steps

1: palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; caesium carbonate / 1,4-dioxane / 4 h / 150 °C / Microwave irradiation

2: sodium hydroxide; water / methanol / Reflux

3: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 5 h / 80 °C

With water; palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; sodium hydroxide; In 1,4-dioxane; methanol; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2014.05.066

upstream raw materials:

4-methoxycarbonyl aniline

2,4-dichloro-5H-pyrrolo[3,2-d]pyrimidine

2,4-dichloro-5-[(4-methylphenyl)sulfonyl]-5H-pyrrolo[3,2-d]pyrimidine

2-chloro-5-p-toluenesulfonyl-4-(4-(trifluoromethoxy)phenyl)-5H-pyrrolo[3,2-d]pyrimidine

Downstream raw materials:

N-(5-(chloromethyl)-2-methylphenyl)-4-((4-(4-(trifluoromethoxy)phenyl)-5H-pyrrolo[3,2-d]pyrimidin-2-yl)amino)benzamide

N-(2-methyl-5-((4-methylpiperazin-1-yl)methyl)phenyl)-4-((4-(4-(trifluoromethoxy)phenyl)-5H-pyrrolo[3,2-d]pyrimidin-2-yl)amino)benzamide

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