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

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Chemical Name:N-(2-methyl-5-((4-methylpiperazin-1-yl)methyl)phenyl)-4-((4-(4-(trifluoromethoxy)phenyl)-6,7-dihydro-5H-pyrano[2,3-d]pyrimidin-2-yl)amino)benzamide
CAS No.:1575815-65-4
Molecular Formula:C₃₄H₃₅F₃N₆O₃
Molecular Weight:632.686
Hs Code.:

Synonyms:N-(2-methyl-5-((4-methylpiperazin-1-yl)methyl)phenyl)-4-((4-(4-(trifluoromethoxy)phenyl)-6,7-dihydro-5H-pyrano[2,3-d]pyrimidin-2-yl)amino)benzamide

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Chemical Property of N-(2-methyl-5-((4-methylpiperazin-1-yl)methyl)phenyl)-4-((4-(4-(trifluoromethoxy)phenyl)-6,7-dihydro-5H-pyrano[2,3-d]pyrimidin-2-yl)amino)benzamide

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Technology Process of N-(2-methyl-5-((4-methylpiperazin-1-yl)methyl)phenyl)-4-((4-(4-(trifluoromethoxy)phenyl)-6,7-dihydro-5H-pyrano[2,3-d]pyrimidin-2-yl)amino)benzamide

There total 10 articles about N-(2-methyl-5-((4-methylpiperazin-1-yl)methyl)phenyl)-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: 71.0%

: 109-01-3
1-methyl-piperazine

: 1575815-64-3
N-(5-(chloromethyl)-2-methylphenyl)-4-((4-(4-(trifluoromethoxy)phenyl)-6,7-dihydro-5H-pyrano[2,3-d]pyrimidin-2-yl)amino)benzamide

: 1575815-65-4
N-(2-methyl-5-((4-methylpiperazin-1-yl)methyl)phenyl)-4-((4-(4-(trifluoromethoxy)phenyl)-6,7-dihydro-5H-pyrano[2,3-d]pyrimidin-2-yl)amino)benzamide

Guidance literature:: With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 6h;
DOI:10.1007/s00044-014-0959-3

Reference yield:

: 542-28-9,26354-94-9
3,4,5,6-tetrahydro-2H-pyran-2-one

: 1575815-65-4
N-(2-methyl-5-((4-methylpiperazin-1-yl)methyl)phenyl)-4-((4-(4-(trifluoromethoxy)phenyl)-6,7-dihydro-5H-pyrano[2,3-d]pyrimidin-2-yl)amino)benzamide

Guidance literature:: Multi-step reaction with 10 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-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 17 h / 80 °C / Inert atmosphere

9: thionyl chloride / dichloromethane / 17 h / 20 °C

10: potassium carbonate / N,N-dimethyl-formamide / 6 h / 20 °C

With bis-triphenylphosphine-palladium(II) chloride; thionyl chloride; trifluoromethylsulfonic anhydride; palladium diacetate; sodium carbonate; potassium carbonate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; 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

Reference yield:

: 946828-44-0
2,4-bis(methylsulfonyl)-6,7-dihydro-5H-pyrano[2,3-d]pyrimidine

: 1575815-65-4
N-(2-methyl-5-((4-methylpiperazin-1-yl)methyl)phenyl)-4-((4-(4-(trifluoromethoxy)phenyl)-6,7-dihydro-5H-pyrano[2,3-d]pyrimidin-2-yl)amino)benzamide

Guidance literature:: Multi-step reaction with 8 steps

1: sodium hydroxide / methanol / 2 h / Reflux

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

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

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

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

6: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 17 h / 80 °C / Inert atmosphere

7: thionyl chloride / dichloromethane / 17 h / 20 °C

8: potassium carbonate / N,N-dimethyl-formamide / 6 h / 20 °C

With bis-triphenylphosphine-palladium(II) chloride; thionyl chloride; palladium diacetate; sodium carbonate; potassium carbonate; 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; trichlorophosphate; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide; 3: |Suzuki-Miyaura Coupling / 4: |Buchwald-Hartwig Coupling;
DOI:10.1007/s00044-014-0959-3