(S)-methyl 5-oxo-5,6,7,8-tetrahydroimidazo[1,5-c]pyrimidine-7-carboxylate

Base Information

• Chemical Name: (S)-methyl 5-oxo-5,6,7,8-tetrahydroimidazo[1,5-c]pyrimidine-7-carboxylate
• CAS No.: 69614-04-6
• Molecular Formula: C8H9N3O3
• Molecular Weight: 195.178
• Mol file: 69614-04-6.mol

Synonyms:(S)-methyl 5-oxo-5,6,7,8-tetrahydroimidazo[1,5-c]pyrimidine-7-carboxylate;NSC 249994;

Chemical Property of (S)-methyl 5-oxo-5,6,7,8-tetrahydroimidazo[1,5-c]pyrimidine-7-carboxylate

Chemical Property:

• Melting Point: 165-167 ℃
• Refractive Index: 1.682
• PSA: 73.22000
• Density: 1.56 g/cm³
• LogP: -0.13270
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (Slightly)

Purity/Quality:

98%min ^*data from raw suppliers

(S)-methyl5-Oxo-5,6,7,8-tetrahydroimidazo[1,5-c]pyrimidine-7-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (S)-methyl 5-Oxo-5,6,7,8-tetrahydroimidazo[1,5-c]pyrimidine-7-carboxylate is a chemical reagent used in the preparation of histidine dehydrogenase inhibitors as anti-infectious agents.

Technology Process of (S)-methyl 5-oxo-5,6,7,8-tetrahydroimidazo[1,5-c]pyrimidine-7-carboxylate

There total 12 articles about (S)-methyl 5-oxo-5,6,7,8-tetrahydroimidazo[1,5-c]pyrimidine-7-carboxylate 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: 85.0%

bis(trichloromethyl) carbonate (32315-10-9) + L-histidine methyl ester dihydrochloride (7389-87-9) → S-(+)-7-Methoxycarbonyl-5,6,7,8-tetrahydroimidazo<1,5-c>pyrimidin-5-on (69614-04-6)

Guidance literature:

L-histidine methyl ester dihydrochloride; With triethylamine; In acetonitrile; at 20 - 30 ℃; for 1h;

bis(trichloromethyl) carbonate; In N,N-dimethyl-formamide; acetonitrile; at 60 - 70 ℃; for 5h;

Reference yield: 82.0%

L-histidine methyl ester dihydrochloride (7389-87-9) + 1,1'-carbonyldiimidazole (530-62-1) → S-(+)-7-Methoxycarbonyl-5,6,7,8-tetrahydroimidazo<1,5-c>pyrimidin-5-on (69614-04-6)

Guidance literature:

at 80 ℃; for 0.5h;

DOI:10.1016/j.tetlet.2005.12.090

Reference yield: 67.0%

l-histidine methyl ester dihydrochloride (4467-54-3,5619-10-3,7389-87-9,18684-16-7,22888-60-4,32381-17-2,92742-29-5,100009-20-9) + 1,1'-carbonyldiimidazole (530-62-1) → S-(+)-7-Methoxycarbonyl-5,6,7,8-tetrahydroimidazo<1,5-c>pyrimidin-5-on (69614-04-6)

Guidance literature:

In N,N-dimethyl-formamide; at 60 ℃; for 12h;

DOI:10.1002/chem.200601420

upstream raw materials:

l-histidine methyl ester dihydrochloride

1,1'-carbonyldiimidazole

L-Histidine methyl ester

L-histidine methyl ester dihydrochloride

Downstream raw materials:

3-benzyl-5-(1⁽³⁾H-imidazol-4-ylmethyl)-imidazolidine-2,4-dione

L-Histidine methyl ester

Refernces

• 1、 -. "NITROGEN-CONTAINING COMPOUND, METHOD FOR MANUFACTURING THE SAME, AND OPTICAL FUNCTIONAL MATERIAL INCLUDING THE SAME". . . Retrieved 2021/08/21.
• 2、 Zhao, Jingjing,Posa, Dheeraj Kumar,Kumar, Vijay,Hoetker, David,Kumar, Amit,Ganesan, Smirthy,Riggs, Daniel W.,Bhatnagar, Aruni,Wempe, Michael F.,Baba, Shahid P.. "Carnosine protects cardiac myocytes against lipid peroxidation products". . p. 123 - 138. Retrieved 2018/11/23.