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

Base Information

• Chemical Name: methyl 4-((4-(4-(trifluoromethoxy)phenyl)-6,7-dihydro-5H-pyrano[2,3-d]pyrimidin-2-yl)amino)benzoate
• CAS No.: 1575815-60-9
• Molecular Formula: C₂₂H₁₈F₃N₃O₄
• Molecular Weight: 445.398

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

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

Chemical Property:

Purity/Quality:

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

There total 7 articles about methyl 4-((4-(4-(trifluoromethoxy)phenyl)-6,7-dihydro-5H-pyrano[2,3-d]pyrimidin-2-yl)amino)benzoate 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: 86.0%

2-chloro-4-(4-(trifluoromethoxy)phenyl)-6,7-dihydro-5H-pyrano[2,3-d]pyrimidine (1575815-59-6) + 4-methoxycarbonyl aniline (619-45-4) → methyl 4-((4-(4-(trifluoromethoxy)phenyl)-6,7-dihydro-5H-pyrano[2,3-d]pyrimidin-2-yl)amino)benzoate (1575815-60-9)

Guidance literature:

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

DOI:10.1007/s00044-014-0959-3

Reference yield:

3,4,5,6-tetrahydro-2H-pyran-2-one (542-28-9,26354-94-9) → methyl 4-((4-(4-(trifluoromethoxy)phenyl)-6,7-dihydro-5H-pyrano[2,3-d]pyrimidin-2-yl)amino)benzoate (1575815-60-9)

Guidance literature:

Multi-step reaction with 6 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

With bis-triphenylphosphine-palladium(II) chloride; trifluoromethylsulfonic anhydride; palladium diacetate; sodium carbonate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; sodium hydroxide; trichlorophosphate; In 1,4-dioxane; methanol; dichloromethane; 5: |Suzuki-Miyaura Coupling / 6: |Buchwald-Hartwig Coupling;

DOI:10.1007/s00044-014-0959-3

Reference yield:

2,4-bis(methylsulfonyl)-6,7-dihydro-5H-pyrano[2,3-d]pyrimidine (946828-44-0) → methyl 4-((4-(4-(trifluoromethoxy)phenyl)-6,7-dihydro-5H-pyrano[2,3-d]pyrimidin-2-yl)amino)benzoate (1575815-60-9)

Guidance literature:

Multi-step reaction with 4 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

With bis-triphenylphosphine-palladium(II) chloride; palladium diacetate; sodium carbonate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; N-ethyl-N,N-diisopropylamine; sodium hydroxide; trichlorophosphate; In 1,4-dioxane; methanol; 3: |Suzuki-Miyaura Coupling / 4: |Buchwald-Hartwig Coupling;

DOI:10.1007/s00044-014-0959-3

upstream raw materials:

2-chloro-4-(4-(trifluoromethoxy)phenyl)-6,7-dihydro-5H-pyrano[2,3-d]pyrimidine

4-methoxycarbonyl aniline

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

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

Downstream raw materials:

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

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

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

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

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