(rac)-2,2,2-trifluoro-N-[{[2-{[6-(4-fluoro-2-methoxyphenyl)pyrimidin-4-yl]amino}-6-(trifluoromethyl)pyridin-4-yl]methyl}(methyl)-λ⁴-sulfanylidene]acetamide

Base Information

• Chemical Name: (rac)-2,2,2-trifluoro-N-[{[2-{[6-(4-fluoro-2-methoxyphenyl)pyrimidin-4-yl]amino}-6-(trifluoromethyl)pyridin-4-yl]methyl}(methyl)-λ⁴-sulfanylidene]acetamide
• CAS No.: 1610462-87-7
• Molecular Formula: C₂₁H₁₆F₇N₅O₂S
• Molecular Weight: 535.445

Synonyms:(rac)-2,2,2-trifluoro-N-[{[2-{[6-(4-fluoro-2-methoxyphenyl)pyrimidin-4-yl]amino}-6-(trifluoromethyl)pyridin-4-yl]methyl}(methyl)-λ⁴-sulfanylidene]acetamide

Chemical Property of (rac)-2,2,2-trifluoro-N-[{[2-{[6-(4-fluoro-2-methoxyphenyl)pyrimidin-4-yl]amino}-6-(trifluoromethyl)pyridin-4-yl]methyl}(methyl)-λ⁴-sulfanylidene]acetamide

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Technology Process of (rac)-2,2,2-trifluoro-N-[{[2-{[6-(4-fluoro-2-methoxyphenyl)pyrimidin-4-yl]amino}-6-(trifluoromethyl)pyridin-4-yl]methyl}(methyl)-λ⁴-sulfanylidene]acetamide

There total 5 articles about (rac)-2,2,2-trifluoro-N-[{[2-{[6-(4-fluoro-2-methoxyphenyl)pyrimidin-4-yl]amino}-6-(trifluoromethyl)pyridin-4-yl]methyl}(methyl)-λ⁴-sulfanylidene]acetamide 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:

2,2,2-trifluoroacetamide (354-38-1) + 6-(4-fluoro-2-methoxyphenyl)-N-{4-[(methylsulfanyl)methyl]-6-(trifluoromethyl)pyridin-2-yl}pyrimidin-4-amine (1603923-12-1) → (rac)-2,2,2-trifluoro-N-[{[2-{[6-(4-fluoro-2-methoxyphenyl)pyrimidin-4-yl]amino}-6-(trifluoromethyl)pyridin-4-yl]methyl}(methyl)-λ4-sulfanylidene]acetamide (1610462-87-7)

Guidance literature:

2,2,2-trifluoroacetamide; With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; sodium t-butanolate; In tetrahydrofuran; at 10 ℃; for 0.166667h; Inert atmosphere;

6-(4-fluoro-2-methoxyphenyl)-N-{4-[(methylsulfanyl)methyl]-6-(trifluoromethyl)pyridin-2-yl}pyrimidin-4-amine; In tetrahydrofuran; at -5 ℃; for 2h; Inert atmosphere;

Reference yield:

2-chloro-4-[(methylsulfanyl)methyl]-6-(trifluoromethyl)pyridine (1602486-13-4) → (rac)-2,2,2-trifluoro-N-[{[2-{[6-(4-fluoro-2-methoxyphenyl)pyrimidin-4-yl]amino}-6-(trifluoromethyl)pyridin-4-yl]methyl}(methyl)-λ4-sulfanylidene]acetamide (1610462-87-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 1-methyl-pyrrolidin-2-one; XPhos; potassium phosphate; chloro(2-dicyclohexylphosphino-2',4',6'-tri-iso-propyl-1,1'-biphenyl)[2-(2-aminoethyl)phenyl]palladium(II) methyl-tert-butyl ether adduct / toluene / 4 h / 130 °C / Inert atmosphere; Sealed tube

2.1: sodium t-butanolate; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / tetrahydrofuran / 0.17 h / 10 °C / Inert atmosphere

2.2: 2 h / -5 °C / Inert atmosphere

With 1-methyl-pyrrolidin-2-one; potassium phosphate; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; chloro(2-dicyclohexylphosphino-2',4',6'-tri-iso-propyl-1,1'-biphenyl)[2-(2-aminoethyl)phenyl]palladium(II) methyl-tert-butyl ether adduct; sodium t-butanolate; XPhos; In tetrahydrofuran; toluene;

Reference yield:

4-fluoro-2-methoxyphenylboronic acid (179899-07-1) → (rac)-2,2,2-trifluoro-N-[{[2-{[6-(4-fluoro-2-methoxyphenyl)pyrimidin-4-yl]amino}-6-(trifluoromethyl)pyridin-4-yl]methyl}(methyl)-λ4-sulfanylidene]acetamide (1610462-87-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; water / 1,2-dimethoxyethane / 2.5 h / 90 °C / Inert atmosphere

2.1: 1-methyl-pyrrolidin-2-one; XPhos; potassium phosphate; chloro(2-dicyclohexylphosphino-2',4',6'-tri-iso-propyl-1,1'-biphenyl)[2-(2-aminoethyl)phenyl]palladium(II) methyl-tert-butyl ether adduct / toluene / 4 h / 130 °C / Inert atmosphere; Sealed tube

3.1: sodium t-butanolate; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / tetrahydrofuran / 0.17 h / 10 °C / Inert atmosphere

3.2: 2 h / -5 °C / Inert atmosphere

With 1-methyl-pyrrolidin-2-one; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; chloro(2-dicyclohexylphosphino-2',4',6'-tri-iso-propyl-1,1'-biphenyl)[2-(2-aminoethyl)phenyl]palladium(II) methyl-tert-butyl ether adduct; water; potassium carbonate; sodium t-butanolate; XPhos; In tetrahydrofuran; 1,2-dimethoxyethane; toluene;

upstream raw materials:

2,2,2-trifluoroacetamide

6-(4-fluoro-2-methoxyphenyl)-N-{4-[(methylsulfanyl)methyl]-6-(trifluoromethyl)pyridin-2-yl}pyrimidin-4-amine

6-(4-fluoro-2-methoxyphenyl)pyrimidin-4-amine

4-(bromomethyl)-2-chloro-6-(trifluoromethyl)pyridine

Downstream raw materials:

(rac)-6-(4-fluoro-2-methoxyphenyl)-N-{4-[(S-methylsulfonimidoyl)methyl]-6-(trifluoromethyl)pyridin-2yl}pyrimidin-4-amine

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