(rac)-[(2,3-difluoro-5-{[5-fluoro-4-(4-fluoro-2-methoxyphenyl)pyrimidin-2-yl]amino}benzyl)(methyl)-λ⁴-sulfanylidene]cyanamide

Base Information

• Chemical Name: (rac)-[(2,3-difluoro-5-{[5-fluoro-4-(4-fluoro-2-methoxyphenyl)pyrimidin-2-yl]amino}benzyl)(methyl)-λ⁴-sulfanylidene]cyanamide
• CAS No.: 1427315-59-0
• Molecular Formula: C₂₀H₁₅F₄N₅OS
• Molecular Weight: 449.432

Synonyms:(rac)-[(2,3-difluoro-5-{[5-fluoro-4-(4-fluoro-2-methoxyphenyl)pyrimidin-2-yl]amino}benzyl)(methyl)-λ⁴-sulfanylidene]cyanamide

Chemical Property of (rac)-[(2,3-difluoro-5-{[5-fluoro-4-(4-fluoro-2-methoxyphenyl)pyrimidin-2-yl]amino}benzyl)(methyl)-λ⁴-sulfanylidene]cyanamide

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Technology Process of (rac)-[(2,3-difluoro-5-{[5-fluoro-4-(4-fluoro-2-methoxyphenyl)pyrimidin-2-yl]amino}benzyl)(methyl)-λ⁴-sulfanylidene]cyanamide

There total 8 articles about (rac)-[(2,3-difluoro-5-{[5-fluoro-4-(4-fluoro-2-methoxyphenyl)pyrimidin-2-yl]amino}benzyl)(methyl)-λ⁴-sulfanylidene]cyanamide 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: 83.0%

CYANAMID (420-04-2) + N-{3,4-difluoro-5-[(methylsulfanyl)methyl]phenyl}-5-fluoro-4-(4-fluoro-2-methoxyphenyl)-pyrimidin-2-amine (1427315-57-8) → (rac)-[(2,3-difluoro-5-{[5-fluoro-4-(4-fluoro-2-methoxyphenyl)pyrimidin-2-yl]amino}benzyl)(methyl)-λ4-sulfanylidene]cyanamide (1427315-59-0)

Guidance literature:

With [bis(acetoxy)iodo]benzene; In dichloromethane; at 0 - 20 ℃; for 4h;

DOI:10.1021/acs.jmedchem.1c01000

Reference yield:

4-fluoro-2-methoxyphenylboronic acid (179899-07-1) → (rac)-[(2,3-difluoro-5-{[5-fluoro-4-(4-fluoro-2-methoxyphenyl)pyrimidin-2-yl]amino}benzyl)(methyl)-λ4-sulfanylidene]cyanamide (1427315-59-0)

Guidance literature:

Multi-step reaction with 3 steps

1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / 1,2-dimethoxyethane / 16 h / 90 °C / Inert atmosphere

2: XPhos; potassium phosphate; chloro(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2-aminoethyl)phenyl]palladium(II) methyl-t-butyl ether adduct / toluene; 1-methyl-pyrrolidin-2-one / 3 h / 130 °C / Inert atmosphere; Sealed tube; Microwave irradiation

3: [bis(acetoxy)iodo]benzene / dichloromethane / 4 h / 0 - 20 °C

With potassium phosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; chloro(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2-aminoethyl)phenyl]palladium(II) methyl-t-butyl ether adduct; [bis(acetoxy)iodo]benzene; potassium carbonate; XPhos; In 1-methyl-pyrrolidin-2-one; 1,2-dimethoxyethane; dichloromethane; toluene;

DOI:10.1021/acs.jmedchem.1c01000

Reference yield:

2-chloro-5-fluoro-4-(4-fluoro-2-methoxyphenyl)pyrimidine (1426215-30-6) → (rac)-[(2,3-difluoro-5-{[5-fluoro-4-(4-fluoro-2-methoxyphenyl)pyrimidin-2-yl]amino}benzyl)(methyl)-λ4-sulfanylidene]cyanamide (1427315-59-0)

Guidance literature:

Multi-step reaction with 2 steps

1: XPhos; potassium phosphate; chloro(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2-aminoethyl)phenyl]palladium(II) methyl-t-butyl ether adduct / toluene; 1-methyl-pyrrolidin-2-one / 3 h / 130 °C / Inert atmosphere; Sealed tube; Microwave irradiation

2: [bis(acetoxy)iodo]benzene / dichloromethane / 4 h / 0 - 20 °C

With potassium phosphate; chloro(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2-aminoethyl)phenyl]palladium(II) methyl-t-butyl ether adduct; [bis(acetoxy)iodo]benzene; XPhos; In 1-methyl-pyrrolidin-2-one; dichloromethane; toluene;

DOI:10.1021/acs.jmedchem.1c01000

upstream raw materials:

4-fluoro-2-methoxyphenylboronic acid

2-chloro-5-fluoro-4-(4-fluoro-2-methoxyphenyl)pyrimidine

CYANAMID

N-{3,4-difluoro-5-[(methylsulfanyl)methyl]phenyl}-5-fluoro-4-(4-fluoro-2-methoxyphenyl)-pyrimidin-2-amine

Downstream raw materials:

(rac)-[(2,3-difluoro-5-{[5-fluoro-4-(4-fluoro-2-methoxyphenyl)pyrimidin-2-yl] amino}benzyl)(methyl)oxido-λ⁶-sulfanylidene]cyanamide

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