N-(2,6-dimethylphenyl)-4-((4-(4-(trifluoromethoxy)phenyl)-6,7-dihydro-5H-pyrano[2,3-d]pyrimidin-2-yl)amino)benzamide

Base Information

• Chemical Name: N-(2,6-dimethylphenyl)-4-((4-(4-(trifluoromethoxy)phenyl)-6,7-dihydro-5H-pyrano[2,3-d]pyrimidin-2-yl)amino)benzamide
• CAS No.: 1575815-62-1
• Molecular Formula: C₂₉H₂₅F₃N₄O₃
• Molecular Weight: 534.538
• Mol file: 1575815-62-1.mol

Synonyms:N-(2,6-dimethylphenyl)-4-((4-(4-(trifluoromethoxy)phenyl)-6,7-dihydro-5H-pyrano[2,3-d]pyrimidin-2-yl)amino)benzamide

Chemical Property of N-(2,6-dimethylphenyl)-4-((4-(4-(trifluoromethoxy)phenyl)-6,7-dihydro-5H-pyrano[2,3-d]pyrimidin-2-yl)amino)benzamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(2,6-dimethylphenyl)-4-((4-(4-(trifluoromethoxy)phenyl)-6,7-dihydro-5H-pyrano[2,3-d]pyrimidin-2-yl)amino)benzamide

There total 9 articles about N-(2,6-dimethylphenyl)-4-((4-(4-(trifluoromethoxy)phenyl)-6,7-dihydro-5H-pyrano[2,3-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: 80.0%

4-((4-(4-(trifluoromethoxy)phenyl)-6,7-dihydro-5H-pyrano[2,3-d]pyrimidin-2-yl)amino)benzoic acid (1575815-61-0) + 2,6-dimethylaniline (87-62-7) → N-(2,6-dimethylphenyl)-4-((4-(4-(trifluoromethoxy)phenyl)-6,7-dihydro-5H-pyrano[2,3-d]pyrimidin-2-yl)amino)benzamide (1575815-62-1)

Guidance literature:

With triethylamine; 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 20 ℃; for 16h; Inert atmosphere;

DOI:10.1007/s00044-014-0959-3

Reference yield: 80.0%

→ N-(2,6-dimethylphenyl)-4-((4-(4-(trifluoromethoxy)phenyl)-6,7-dihydro-5H-pyrano[2,3-d]pyrimidin-2-yl)amino)benzamide (1575815-62-1)

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 16h;

Reference yield:

3,4,5,6-tetrahydro-2H-pyran-2-one (542-28-9,26354-94-9) → N-(2,6-dimethylphenyl)-4-((4-(4-(trifluoromethoxy)phenyl)-6,7-dihydro-5H-pyrano[2,3-d]pyrimidin-2-yl)amino)benzamide (1575815-62-1)

Guidance literature:

Multi-step reaction with 8 steps

1: trifluoromethylsulfonic anhydride / dichloromethane / 42 h / -78 - 0 °C

2: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 5 h / 20 °C

3: sodium hydroxide / methanol / 2 h / Reflux

4: N-ethyl-N,N-diisopropylamine; trichlorophosphate / 18 h / Reflux

5: sodium carbonate; bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane / 2 h / Reflux; Inert atmosphere

6: palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; caesium carbonate / 1,4-dioxane / 13 h / Reflux; Inert atmosphere

7: sodium hydroxide / methanol; tetrahydrofuran / 5 h / Reflux

8: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 16 h / 20 °C / Inert atmosphere

With bis-triphenylphosphine-palladium(II) chloride; trifluoromethylsulfonic anhydride; palladium diacetate; sodium carbonate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; sodium hydroxide; trichlorophosphate; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide; 5: |Suzuki-Miyaura Coupling / 6: |Buchwald-Hartwig Coupling;

DOI:10.1007/s00044-014-0959-3

upstream raw materials:

4-((4-(4-(trifluoromethoxy)phenyl)-6,7-dihydro-5H-pyrano[2,3-d]pyrimidin-2-yl)amino)benzoic acid

2,6-dimethylaniline

3,4,5,6-tetrahydro-2H-pyran-2-one

2,4-bis(methylthio)-6,7-dihydro-5H-pyrano[2,3-d]pyrimidine