4-chloro-7-[2-fluoro-4-(methylsulfonyl)phenyl]-2-methyl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine

Base Information

• Chemical Name: 4-chloro-7-[2-fluoro-4-(methylsulfonyl)phenyl]-2-methyl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine
• CAS No.: 1001397-52-9
• Molecular Formula: C₁₄H₁₃ClFN₃O₂S
• Molecular Weight: 341.794
• Mol file: 1001397-52-9.mol

Synonyms:4-chloro-7-[2-fluoro-4-(methylsulfonyl)phenyl]-2-methyl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine

Chemical Property of 4-chloro-7-[2-fluoro-4-(methylsulfonyl)phenyl]-2-methyl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-chloro-7-[2-fluoro-4-(methylsulfonyl)phenyl]-2-methyl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine

There total 6 articles about 4-chloro-7-[2-fluoro-4-(methylsulfonyl)phenyl]-2-methyl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine 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: 94.0%

2-(4-chloro-6-{{[(1,1-dimethylethyl)oxy]carbonyl}[2-fluoro-4-(methylsulfonyl)phenyl]amino}-2-methyl-5-pyrimidinyl)ethyl methanesulfonate (1001397-51-8) → 4-chloro-7-[2-fluoro-4-(methylsulfonyl)phenyl]-2-methyl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine (1001397-52-9)

Guidance literature:

2-(4-chloro-6-{{[(1,1-dimethylethyl)oxy]carbonyl}[2-fluoro-4-(methylsulfonyl)phenyl]amino}-2-methyl-5-pyrimidinyl)ethyl methanesulfonate; With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 3h;

With triethylamine; In dichloromethane; at 20 ℃; for 18h;

Reference yield:

C14H15ClFN3O3S → 4-chloro-7-[2-fluoro-4-(methylsulfonyl)phenyl]-2-methyl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine (1001397-52-9)

Guidance literature:

With triethylamine; Methanesulfonic anhydride; In dichloromethane; at 5 - 20 ℃; for 15h;

DOI:10.1021/jm301404a

Reference yield:

(2-propenyl)propanedioic acid diethyl ester (2049-80-1) → 4-chloro-7-[2-fluoro-4-(methylsulfonyl)phenyl]-2-methyl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine (1001397-52-9)

Guidance literature:

Multi-step reaction with 5 steps

1: sodium methylate / methanol / 37 h / 20 °C / Inert atmosphere

2: trichlorophosphate / 4 h / Inert atmosphere; Reflux

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

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

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

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

DOI:10.1021/jm301404a

upstream raw materials:

2-(4-chloro-6-{{[(1,1-dimethylethyl)oxy]carbonyl}[2-fluoro-4-(methylsulfonyl)phenyl]amino}-2-methyl-5-pyrimidinyl)ethyl methanesulfonate

(2-propenyl)propanedioic acid diethyl ester

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

5-Allyl-2-methyl-4,6-dichloropyrimidine

Downstream raw materials:

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

7-[2-fluoro-4-(methylsulfonyl)phenyl]-2-methyl-4-({1-[3-(1-methylethyl)-1,2,4-oxadiazol-5-yl]-4-piperidinyl}oxy)-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine

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

Refernces

• 1、 -. "GPR119 AGONISTS FOR THE TREATMENT OF DIABETES AND RELATED DISORDERS". Page/Page column 82; 83. . Retrieved 2010/11/29.