2-amino-7-[2-fluoro-4-(methylsulfonyl)phenyl]-1,5,6,7-tetrahydro-4H-pyrrolo[2,3-d]pyrimidin-4-one

Base Information

• Chemical Name: 2-amino-7-[2-fluoro-4-(methylsulfonyl)phenyl]-1,5,6,7-tetrahydro-4H-pyrrolo[2,3-d]pyrimidin-4-one
• CAS No.: 1001399-56-9
• Molecular Formula: C₁₃H₁₃FN₄O₃S
• Molecular Weight: 324.336
• Mol file: 1001399-56-9.mol

Synonyms:2-amino-7-[2-fluoro-4-(methylsulfonyl)phenyl]-1,5,6,7-tetrahydro-4H-pyrrolo[2,3-d]pyrimidin-4-one

Chemical Property of 2-amino-7-[2-fluoro-4-(methylsulfonyl)phenyl]-1,5,6,7-tetrahydro-4H-pyrrolo[2,3-d]pyrimidin-4-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-amino-7-[2-fluoro-4-(methylsulfonyl)phenyl]-1,5,6,7-tetrahydro-4H-pyrrolo[2,3-d]pyrimidin-4-one

There total 6 articles about 2-amino-7-[2-fluoro-4-(methylsulfonyl)phenyl]-1,5,6,7-tetrahydro-4H-pyrrolo[2,3-d]pyrimidin-4-one 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:

methyl 1-[2-fluoro-4-(methylsulfonyl)phenyl]-2-thioxo-3-pyrrolidinecarboxylate (1001399-55-8) + guanidine hydrochloride (50-01-1) → 2-amino-7-[2-fluoro-4-(methylsulfonyl)phenyl]-1,5,6,7-tetrahydro-4H-pyrrolo[2,3-d]pyrimidin-4-one (1001399-56-9)

Guidance literature:

guanidine hydrochloride; With sodium methylate; In methanol; at 20 ℃; for 0.5h;

methyl 1-[2-fluoro-4-(methylsulfonyl)phenyl]-2-thioxo-3-pyrrolidinecarboxylate; In methanol; at 60 - 90 ℃; for 1.08333h;

With hydrogenchloride; In methanol; water; at 20 ℃; for 18h; pH=6;

Reference yield:

methyl 1-[2-fluoro-4-(methylsulfonyl)phenyl]-2-oxo-3-pyrrolidinecarboxylate (1001399-54-7) + guanidine hydrochloride (50-01-1) → 2-amino-7-[2-fluoro-4-(methylsulfonyl)phenyl]-1,5,6,7-tetrahydro-4H-pyrrolo[2,3-d]pyrimidin-4-one (1001399-56-9)

Guidance literature:

guanidine hydrochloride; With sodium methylate; In methanol; at 20 ℃; for 0.5h; Inert atmosphere;

methyl 1-[2-fluoro-4-(methylsulfonyl)phenyl]-2-oxo-3-pyrrolidinecarboxylate; In methanol; at 60 - 90 ℃; for 1h;

DOI:10.1021/jm301404a

Reference yield:

6-hydroxy-5-(2-propen-1-yl)-4(1H)-pyrimidinone (16019-30-0) → 2-amino-7-[2-fluoro-4-(methylsulfonyl)phenyl]-1,5,6,7-tetrahydro-4H-pyrrolo[2,3-d]pyrimidin-4-one (1001399-56-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: trichlorophosphate / 4 h / Inert atmosphere; Reflux

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

3.1: acetonitrile / 3 h / 60 °C / Inert atmosphere

3.2: 5 h / 70 °C

4.1: sulfuric acid / methanol / 2 h / Reflux

5.1: sodium methylate / methanol / 0.5 h / 20 °C / Inert atmosphere

5.2: 1 h / 60 - 90 °C

With sulfuric acid; sodium methylate; sodium hydride; trichlorophosphate; In tetrahydrofuran; methanol; acetonitrile;

DOI:10.1021/jm301404a

upstream raw materials:

methyl 1-[2-fluoro-4-(methylsulfonyl)phenyl]-2-thioxo-3-pyrrolidinecarboxylate

guanidine hydrochloride

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

5-allyl-4,6-dichloropyrimidine

Downstream raw materials:

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

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

Refernces

• 1、 -. "GPR119 AGONISTS FOR THE TREATMENT OF DIABETES AND RELATED DISORDERS". Page/Page column 180; 181. . Retrieved 2010/11/29.