ethyl 4-({7-[2-fluoro-4-(methylsulfonyl)phenyl]-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl}oxy)-1-piperidinecarboxylate

Base Information

• Chemical Name: ethyl 4-({7-[2-fluoro-4-(methylsulfonyl)phenyl]-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl}oxy)-1-piperidinecarboxylate
• CAS No.: 1001398-47-5
• Molecular Formula: C₂₁H₂₅FN₄O₅S
• Molecular Weight: 464.518

Synonyms:ethyl 4-({7-[2-fluoro-4-(methylsulfonyl)phenyl]-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl}oxy)-1-piperidinecarboxylate

Chemical Property of ethyl 4-({7-[2-fluoro-4-(methylsulfonyl)phenyl]-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl}oxy)-1-piperidinecarboxylate

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Technology Process of ethyl 4-({7-[2-fluoro-4-(methylsulfonyl)phenyl]-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl}oxy)-1-piperidinecarboxylate

There total 7 articles about ethyl 4-({7-[2-fluoro-4-(methylsulfonyl)phenyl]-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl}oxy)-1-piperidinecarboxylate 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: 91.0%

1,1-dimethylethyl 4-({7-[2-fluoro-4-(methylsulfonyl)phenyl]-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl}oxy)-1-piperidinecarboxylate (1001397-21-2) + chloroformic acid ethyl ester (541-41-3) → ethyl 4-({7-[2-fluoro-4-(methylsulfonyl)phenyl]-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl}oxy)-1-piperidinecarboxylate (1001398-47-5)

Guidance literature:

1,1-dimethylethyl 4-({7-[2-fluoro-4-(methylsulfonyl)phenyl]-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl}oxy)-1-piperidinecarboxylate; With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 2h;

chloroformic acid ethyl ester; With triethylamine; In dichloromethane; at 20 ℃; for 18h;

DOI:10.1021/jm301404a

Reference yield:

6-hydroxy-5-(2-propen-1-yl)-4(1H)-pyrimidinone (16019-30-0) → ethyl 4-({7-[2-fluoro-4-(methylsulfonyl)phenyl]-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl}oxy)-1-piperidinecarboxylate (1001398-47-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: trichlorophosphate / 4 h / Inert atmosphere; Reflux

2.1: sodium hydride / tetrahydrofuran / 3 h / Inert atmosphere; Reflux

3.1: ozone / dichloromethane; methanol / -78 - 20 °C / Inert atmosphere

4.1: triethylamine; Methanesulfonic anhydride / dichloromethane / 15 h / 5 - 20 °C

5.1: sodium hydride / tetrahydrofuran / 0.5 h / Reflux

5.2: 1.5 h / 20 °C / Reflux

6.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C

6.2: 18 h / 20 °C

With sodium hydride; ozone; triethylamine; trifluoroacetic acid; trichlorophosphate; Methanesulfonic anhydride; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jm301404a

Reference yield:

5-allyl-4,6-dichloropyrimidine (16019-31-1) → ethyl 4-({7-[2-fluoro-4-(methylsulfonyl)phenyl]-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl}oxy)-1-piperidinecarboxylate (1001398-47-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: sodium hydride / tetrahydrofuran / 3 h / Inert atmosphere; Reflux

2.1: ozone / dichloromethane; methanol / -78 - 20 °C / Inert atmosphere

3.1: triethylamine; Methanesulfonic anhydride / dichloromethane / 15 h / 5 - 20 °C

4.1: sodium hydride / tetrahydrofuran / 0.5 h / Reflux

4.2: 1.5 h / 20 °C / Reflux

5.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C

5.2: 18 h / 20 °C

With sodium hydride; ozone; triethylamine; trifluoroacetic acid; Methanesulfonic anhydride; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jm301404a

upstream raw materials:

6-hydroxy-5-(2-propen-1-yl)-4(1H)-pyrimidinone

5-allyl-4,6-dichloropyrimidine

6-chloro-N-[2-fluoro-4-(methylsulfonyl)phenyl]-5-(2-propen-1-yl)-4-pyrimidinamine

2-(4-chloro-6-((2-fluoro-4-methanesulfonylphenyl)amino)pyrimidin-5-yl)ethanol

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