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

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Chemical Name:2-[4-(2-chloro-5-ethoxy-4-methoxy-phenyl)-5-cyano-7H-pyrrolo[2,3-d]pyrimidin-2-ylsulfanyl]-N-cyclopropyl-acetamide
CAS No.:1131802-47-5
Molecular Formula:C₂₁H₂₀ClN₅O₃S
Molecular Weight:457.941
Hs Code.:

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

There total 11 articles about 2-[4-(2-chloro-5-ethoxy-4-methoxy-phenyl)-5-cyano-7H-pyrrolo[2,3-d]pyrimidin-2-ylsulfanyl]-N-cyclopropyl-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: 41.0%

: C₂₇H₃₄ClN₅O₄SSi

: 1131802-47-5
2-[4-(2-chloro-5-ethoxy-4-methoxy-phenyl)-5-cyano-7H-pyrrolo[2,3-d]pyrimidin-2-ylsulfanyl]-N-cyclopropyl-acetamide

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

Reference yield:

: 57564-94-0
2-(methylthio)-4-chloropyrrolo<2,3-d>pyrimidine

: 1131802-47-5
2-[4-(2-chloro-5-ethoxy-4-methoxy-phenyl)-5-cyano-7H-pyrrolo[2,3-d]pyrimidin-2-ylsulfanyl]-N-cyclopropyl-acetamide

Guidance literature:: Multi-step reaction with 13 steps

1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 1.5 h / 0 - 20 °C

2.1: N-Bromosuccinimide / N,N-dimethyl-formamide / -78 - 20 °C

3.1: n-butyllithium / hexane; tetrahydrofuran / 0.03 h / -78 °C

3.2: -78 - 20 °C

4.1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 0.17 h

4.2: 0.25 h / 20 °C

5.1: triethylamine; trifluoroacetic anhydride / dichloromethane / 0 - 20 °C

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

7.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / 0 - 20 °C

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

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

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

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

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

13.1: ethylenediamine; tetrabutyl ammonium fluoride / tetrahydrofuran / 40 °C

With bis-triphenylphosphine-palladium(II) chloride; N-Bromosuccinimide; n-butyllithium; oxalyl dichloride; 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; N,N-dimethyl-formamide; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic anhydride; sodium hydroxide; In tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; isopropyl alcohol; acetonitrile; mineral oil;
DOI:10.1016/j.bmc.2012.08.050

Reference yield:

: 1131803-37-6
4-[2-chloro-4-methoxy-5-(2-methoxy-ethoxymethoxy)-phenyl]-2-methylsulfanyl-7-(2-trimethylsilanyl-ethoxymethyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

: 1131802-47-5
2-[4-(2-chloro-5-ethoxy-4-methoxy-phenyl)-5-cyano-7H-pyrrolo[2,3-d]pyrimidin-2-ylsulfanyl]-N-cyclopropyl-acetamide

Guidance literature:: Multi-step reaction with 7 steps

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

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

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

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

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

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

7: ethylenediamine; tetrabutyl ammonium fluoride / tetrahydrofuran / 40 °C

With tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; sodium hydride; caesium carbonate; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; ethylenediamine; triethylamine; 3-chloro-benzenecarboperoxoic acid; sodium hydroxide; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; isopropyl alcohol; acetonitrile; mineral oil;
DOI:10.1016/j.bmc.2012.08.050