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

Base Information

Chemical Name:2-[4-(2-chloro-5-ethoxy-4-methoxy-phenyl)-5-cyano-7H-pyrrolo[2,3-d]pyrimidin-2-ylsulfanyl]-N-ethyl-acetamide
CAS No.:1131802-63-5
Molecular Formula:C₂₀H₂₀ClN₅O₃S
Molecular Weight:445.929
Hs Code.:

Synonyms: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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Chemical Property of 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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Technology Process of 2-[4-(2-chloro-5-ethoxy-4-methoxy-phenyl)-5-cyano-7H-pyrrolo[2,3-d]pyrimidin-2-ylsulfanyl]-N-ethyl-acetamide

There total 14 articles about 2-[4-(2-chloro-5-ethoxy-4-methoxy-phenyl)-5-cyano-7H-pyrrolo[2,3-d]pyrimidin-2-ylsulfanyl]-N-ethyl-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: 26.0%

: C₂₆H₃₄ClN₅O₄SSi

: 1131802-63-5
2-[4-(2-chloro-5-ethoxy-4-methoxy-phenyl)-5-cyano-7H-pyrrolo[2,3-d]pyrimidin-2-ylsulfanyl]-N-ethyl-acetamide

Guidance literature:: With tetrabutyl ammonium fluoride; ethylenediamine; In tetrahydrofuran; at 40 ℃; Inert atmosphere;
DOI:10.1016/j.bmc.2012.08.050

Reference yield:

: 37942-01-1
5-bromo-2-methoxyphenol

: 1131802-63-5
2-[4-(2-chloro-5-ethoxy-4-methoxy-phenyl)-5-cyano-7H-pyrrolo[2,3-d]pyrimidin-2-ylsulfanyl]-N-ethyl-acetamide

Guidance literature:: Multi-step reaction with 11 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

7: sodium hydroxide / water; methanol / 2 h / 20 °C

8: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine / tetrahydrofuran; acetonitrile / 1 h / 20 °C

9: pyridinium p-toluenesulfonate / isopropyl alcohol / 80 °C / Inert atmosphere

10: caesium carbonate / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere

11: ethylenediamine; tetrabutyl ammonium fluoride / tetrahydrofuran / 40 °C / Inert atmosphere

With bis-triphenylphosphine-palladium(II) chloride; N-chloro-succinimide; n-butyllithium; Triisopropyl borate; phosphorus pentoxide; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; sodium hydride; sodium hydrogencarbonate; caesium carbonate; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; ethylenediamine; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; sodium hydroxide; In tetrahydrofuran; methanol; hexane; dichloromethane; chloroform; water; N,N-dimethyl-formamide; isopropyl alcohol; acetonitrile; mineral oil; 4: |Suzuki Coupling;
DOI:10.1016/j.bmc.2012.08.050

Reference yield:

: C₂₄H₃₀ClN₅O₄SSi

: 1131802-63-5
2-[4-(2-chloro-5-ethoxy-4-methoxy-phenyl)-5-cyano-7H-pyrrolo[2,3-d]pyrimidin-2-ylsulfanyl]-N-ethyl-acetamide

Guidance literature:: Multi-step reaction with 2 steps

1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere

2: ethylenediamine; tetrabutyl ammonium fluoride / tetrahydrofuran / 40 °C / Inert atmosphere

With tetrabutyl ammonium fluoride; caesium carbonate; ethylenediamine; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1016/j.bmc.2012.08.050