[4-(2-chloro-4-methoxy-5-methoxymethoxyphenyl)-5-cyano-7-(2-trimethylsilanylethoxymethyl)-7H-pyrrolo[2,3-d]pyrimidin-2-ylsulfanyl]acetic acid ethyl ester

Base Information

• Chemical Name: [4-(2-chloro-4-methoxy-5-methoxymethoxyphenyl)-5-cyano-7-(2-trimethylsilanylethoxymethyl)-7H-pyrrolo[2,3-d]pyrimidin-2-ylsulfanyl]acetic acid ethyl ester
• CAS No.: 950662-58-5
• Molecular Formula: C₂₆H₃₃ClN₄O₆SSi
• Molecular Weight: 593.176

Synonyms:[4-(2-chloro-4-methoxy-5-methoxymethoxyphenyl)-5-cyano-7-(2-trimethylsilanylethoxymethyl)-7H-pyrrolo[2,3-d]pyrimidin-2-ylsulfanyl]acetic acid ethyl ester

Chemical Property of [4-(2-chloro-4-methoxy-5-methoxymethoxyphenyl)-5-cyano-7-(2-trimethylsilanylethoxymethyl)-7H-pyrrolo[2,3-d]pyrimidin-2-ylsulfanyl]acetic acid ethyl ester

Chemical Property:

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Technology Process of [4-(2-chloro-4-methoxy-5-methoxymethoxyphenyl)-5-cyano-7-(2-trimethylsilanylethoxymethyl)-7H-pyrrolo[2,3-d]pyrimidin-2-ylsulfanyl]acetic acid ethyl ester

There total 13 articles about [4-(2-chloro-4-methoxy-5-methoxymethoxyphenyl)-5-cyano-7-(2-trimethylsilanylethoxymethyl)-7H-pyrrolo[2,3-d]pyrimidin-2-ylsulfanyl]acetic acid ethyl ester 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: 96.0%

4-(2-chloro-4-methoxy-5-methoxymethoxyphenyl)-2-methanesulfonyl-7-(2-trimethylsilanylethoxymethyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile (950662-46-1) + ethyl 2-sulfanylacetate (623-51-8) → [4-(2-chloro-4-methoxy-5-methoxymethoxyphenyl)-5-cyano-7-(2-trimethylsilanylethoxymethyl)-7H-pyrrolo[2,3-d]pyrimidin-2-ylsulfanyl]acetic acid ethyl ester (950662-58-5)

Guidance literature:

ethyl 2-sulfanylacetate; With sodium hydride; In tetrahydrofuran; at 0 ℃;

4-(2-chloro-4-methoxy-5-methoxymethoxyphenyl)-2-methanesulfonyl-7-(2-trimethylsilanylethoxymethyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile; In tetrahydrofuran; at 0 - 20 ℃;

Reference yield: 81.0%

→ [4-(2-chloro-4-methoxy-5-methoxymethoxyphenyl)-5-cyano-7-(2-trimethylsilanylethoxymethyl)-7H-pyrrolo[2,3-d]pyrimidin-2-ylsulfanyl]acetic acid ethyl ester (950662-58-5)

Guidance literature:

Reference yield:

5-bromo-2-methoxyphenol (37942-01-1) → [4-(2-chloro-4-methoxy-5-methoxymethoxyphenyl)-5-cyano-7-(2-trimethylsilanylethoxymethyl)-7H-pyrrolo[2,3-d]pyrimidin-2-ylsulfanyl]acetic acid ethyl ester (950662-58-5)

Guidance literature:

Multi-step reaction with 6 steps

1: trifluoroacetic acid; N-chloro-succinimide / acetonitrile / 16 h / 20 °C

2: phosphorus pentoxide / chloroform / 0 - 20 °C / Inert atmosphere

3: n-butyllithium; Triisopropyl borate / hexane; tetrahydrofuran / -78 - 20 °C / Inert atmosphere

4: bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate / N,N-dimethyl-formamide; water / 1.5 h / 80 °C / Inert atmosphere

5: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / 0 - 20 °C

6: sodium hydride / mineral oil; tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere

With bis-triphenylphosphine-palladium(II) chloride; N-chloro-succinimide; n-butyllithium; Triisopropyl borate; phosphorus pentoxide; sodium hydride; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; In tetrahydrofuran; hexane; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetonitrile; mineral oil; 4: |Suzuki Coupling;

DOI:10.1016/j.bmc.2012.08.050

upstream raw materials:

4-(2-chloro-4-methoxy-5-methoxymethoxyphenyl)-2-methanesulfonyl-7-(2-trimethylsilanylethoxymethyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

ethyl 2-sulfanylacetate

2-(methylthio)-4-chloropyrrolo<2,3-d>pyrimidine

5-bromo-4-chloro-2-methylsulfanyl-7-(2-trimethylsilanylethoxymethyl)-7H-pyrrolo[2,3-d]pyrimidine

Downstream raw materials:

[4-(2-chloro-4-methoxy-5-methoxymethoxyphenyl)-5-cyano-7-(2-trimethylsilanylethoxymethyl)-7H-pyrrolo[2,3-d]pyrimidin-2-ylsulfanyl]acetic acid

2-[4-(2-chloro-5-hydroxy-4-methoxy-phenyl)-5-cyano-7H-pyrrolo[2,3-d]pyrimidin-2-ylsulfanyl]-N-isopropyl-acetamide

2-[4-(2-chloro-4,5-dimethoxy-phenyl)-5-cyano-7H-pyrrolo[2,3-d]pyrimidin-2-ylsulfanyl]-N-ethyl-acetamide

2-[4-(2-chloro-5-ethoxy-4-methoxy-phenyl)-5-cyano-7H-pyrrolo[2,3-d]pyrimidin-2-ylsulfanyl]-N-ethyl-acetamide

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