rac-3-methoxy-1,5-dimethyl-5-(3-nitro-phenyl)-5,6-dihydro-1H-pyrazin-2-one

Base Information

• Chemical Name: rac-3-methoxy-1,5-dimethyl-5-(3-nitro-phenyl)-5,6-dihydro-1H-pyrazin-2-one
• CAS No.: 1350523-47-5
• Molecular Formula: C₁₃H₁₅N₃O₄
• Molecular Weight: 277.28
• Mol file: 1350523-47-5.mol

Synonyms:rac-3-methoxy-1,5-dimethyl-5-(3-nitro-phenyl)-5,6-dihydro-1H-pyrazin-2-one

Chemical Property of rac-3-methoxy-1,5-dimethyl-5-(3-nitro-phenyl)-5,6-dihydro-1H-pyrazin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of rac-3-methoxy-1,5-dimethyl-5-(3-nitro-phenyl)-5,6-dihydro-1H-pyrazin-2-one

There total 10 articles about rac-3-methoxy-1,5-dimethyl-5-(3-nitro-phenyl)-5,6-dihydro-1H-pyrazin-2-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: 79.0%

rac-1,5-dimethyl-5-(3-nitro-phenyl)-piperazine-2,3-dione (1350523-46-4) + trimethoxonium tetrafluoroborate (420-37-1) → rac-3-methoxy-1,5-dimethyl-5-(3-nitro-phenyl)-5,6-dihydro-1H-pyrazin-2-one (1350523-47-5)

Guidance literature:

In dichloromethane; at 20 ℃; for 72h;

DOI:10.1016/j.bmcl.2011.10.050

Reference yield:

rac-2-amino-2-(3-nitro-phenyl)-propan-1-ol (1270385-54-0) → rac-3-methoxy-1,5-dimethyl-5-(3-nitro-phenyl)-5,6-dihydro-1H-pyrazin-2-one (1350523-47-5)

Guidance literature:

Multi-step reaction with 7 steps

1: sodium hydrogencarbonate / tetrahydrofuran / 0 - 20 °C

2: Dess-Martin periodane / dichloromethane / 1 h / 0 - 20 °C

3: acetic acid / tetrahydrofuran; dichloromethane / 1 h / 20 °C

4: sodium triacetoxy borohydride / 2 h / 20 °C

5: N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 0 °C

6: hydrogenchloride / 1,4-dioxane / 1 h / 20 °C

7: dichloromethane / 72 h / 20 °C

With sodium triacetoxy borohydride; hydrogenchloride; sodium hydrogencarbonate; Dess-Martin periodane; acetic acid; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; 1,4-dioxane; dichloromethane;

DOI:10.1016/j.bmcl.2011.10.050

Reference yield:

rac-[1-methyl-2-methylamino-1-(3-nitro-phenyl)-ethyl]-carbamic acid tert-butyl ester (1350523-45-3) → rac-3-methoxy-1,5-dimethyl-5-(3-nitro-phenyl)-5,6-dihydro-1H-pyrazin-2-one (1350523-47-5)

Guidance literature:

Multi-step reaction with 3 steps

1: N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 0 °C

2: hydrogenchloride / 1,4-dioxane / 1 h / 20 °C

3: dichloromethane / 72 h / 20 °C

With hydrogenchloride; N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; dichloromethane;

DOI:10.1016/j.bmcl.2011.10.050

upstream raw materials:

rac-2-amino-2-(3-nitro-phenyl)-propan-1-ol

rac-[1-methyl-1-(3-nitro-phenyl)-2-oxo-ethyl]-carbamic acid tert-butyl ester

rac-[1-methyl-2-methylamino-1-(3-nitro-phenyl)-ethyl]-carbamic acid tert-butyl ester

rac-1,5-dimethyl-5-(3-nitro-phenyl)-piperazine-2,3-dione

Downstream raw materials:

rac-3-amino-1,5-dimethyl-5-(3-nitro-phenyl)-5,6-dihydro-1H-pyrazin-2-one

rac-3-amino-5-(3-amino-phenyl)-1,5-dimethyl-5,6-dihydro-1H-pyrazin-2-one

rac-5-chloro-pyridine-2-carboxylic acid[3-(6-amino-2,4-dimethyl-5-oxo-2,3,4,5-tetrahydro-pyrazin-2-yl)-phenyl]-amide