69614-04-6

Basic information

• Product Name: (S)-methyl 5-oxo-5,6,7,8-tetrahydroimidazo[1,5-c]pyrimidine-7-carboxylate
• Synonyms: (S)-methyl 5-oxo-5,6,7,8-tetrahydroimidazo[1,5-c]pyrimidine-7-carboxylate;Methyl (S)-5,6,7,8-tetrahydro-5-oxoimidazo[1,5-c]pyrimidine-7-carboxylate;NSC 249994;IMidazo[1,5-c]pyriMidine-7-carboxylic acid, 5,6,7,8-tetrahydro-5-oxo-, Methyl ester, (7S)-;METHYL 5-OXO-7,8-DIHYDRO-6H-IMIDAZO[1,5-C]PYRIMIDINE-7-CARBOXYLATE;(S)-methyl 5-oxo-5,6,7,8-tetrahydroimidazo[1,5-f]pyrimidine-7-carboxylate
• CAS NO: 69614-04-6
• Molecular Formula: C₈H₉N₃O₃
• Molecular Weight: 195.18
• Mol File: 69614-04-6.mol
• Article Data: 17

Chemical Properties

• Melting Point: 165-167℃
• Appearance: /
• Density: 1.56
• Refractive Index: 1.682
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: (S)-methyl 5-oxo-5,6,7,8-tetrahydroimidazo[1,5-c]pyrimidine-7-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-methyl 5-oxo-5,6,7,8-tetrahydroimidazo[1,5-c]pyrimidine-7-carboxylate(69614-04-6)
• EPA Substance Registry System: (S)-methyl 5-oxo-5,6,7,8-tetrahydroimidazo[1,5-c]pyrimidine-7-carboxylate(69614-04-6)

Safety Data

• Hazardous Substances Data: 69614-04-6(Hazardous Substances Data)

Usage

Description

(S)-methyl 5-oxo-5,6,7,8-tetrahydroimidazo[1,5-c]pyrimidine-7-carboxylate is an organic compound with a complex chemical structure. It is characterized by its unique molecular arrangement and properties, which make it a valuable compound in various applications.

Uses

Used in Pharmaceutical Industry:
(S)-methyl 5-oxo-5,6,7,8-tetrahydroimidazo[1,5-c]pyrimidine-7-carboxylate is used as a chemical reagent for the preparation of histidine dehydrogenase inhibitors. These inhibitors play a crucial role in the development of anti-infectious agents, as they help combat various infectious diseases by targeting the enzymes involved in the pathogens' metabolism.
Application Reason:
(S)-methyl 5-oxo-5,6,7,8-tetrahydroimidazo[1,5-c]pyrimidine-7-carboxylate's ability to inhibit histidine dehydrogenase makes it a valuable tool in the fight against infectious diseases. By disrupting the metabolic pathways of pathogens, these inhibitors can effectively reduce the growth and proliferation of harmful microorganisms, leading to the development of more effective treatments for a wide range of infections.

InChI:InChI=1/C8H9N3O3/c1-14-7(12)6-2-5-3-9-4-11(5)8(13)10-6/h3-4,6H,2H2,1H3,(H,10,13)

Upstream product

• 13464-19-2 phenyl chlorothioformate 
• 121-44-8 triethylamine 
• 530-62-1 1,1'-carbonyldiimidazole 
• 1499-46-3 L-histidine methyl ester 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 7389-87-9 L-histidine methyl ester dihydrochloride 
• 67-56-1 methanol 
• 71-00-1 L-histidine 
• 124-38-9 carbon dioxide 
• 1499-46-3 L-Histidine methyl ester 
• 4467-54-3 histidine methyl ester hydrochloride 
• 37868-93-2 1,1'-carbonyldiimidazole 
• 71-00-1 L-histidine 
• 4467-54-3 l-histidine methyl ester dihydrochloride 

Downstream Products

• 110182-71-3 3-benzyl-5-(1⁽³⁾H-imidazol-4-ylmethyl)-imidazolidine-2,4-dione 
• 1499-46-3 L-Histidine methyl ester 
• 57519-09-2 (S)-methyl 2-amino-3-(1-methyl-1H-imidazol-4-yl)propanoate 
• 1415221-83-8 N--Fmoc--(2S)--2--amino--3--(1--(8--phenyloctyl)--1H--imidazol--4--yl)propanoic acid 

Relevant articles and documents

(S)-Histidine: The ideal precursor for a novel family of chiral aminoacid and peptidic ionic liquids

(S)-Histidine is shown to be a powerful chiral precursor for the construction of a new series of imidazolium-containing chiral ionic liquids, in which the chiral bifunctional unit of the aminoacid remains unchanged. These ionic materials can be used as building blocks for the synthesis of peptidic ionic liquids.

A Stereoselective Tyrosinase Model Compound Derived from an m-Xylyl- l -histidine Ligand

The aim of mimicking enzyme activity represents an important motivation for the development of new catalysts. A challenging objective is the development of chiral complexes for bioinspired enantioselective oxidation reactions. Herein, we report a new chiral dinuclear copper(II) complex based on a m-xylyl-bis(histidine) ligand (mXHI) as a biomimetic catalyst for tyrosinase and catechol oxidase. The new ligand improves a previous system also containing two tridentate N3 units derived from l-histidine that were connected by a short, rigid ethanediamine bridge. In mXHI the bridge is provided by the more extended m-xylyl moiety. The dicopper(II) complex [Cu2(mXHI)]4+ was studied as a catalyst for stereoselective oxidations of enantiomeric couples of chiral catechols of biological interest (L/D-dopa, L/D-dopa methyl ester, and (R/S)-norepinephrine), showing excellent discrimination capability, particularly for the methyl esters of dopa enantiomers. The catechol oxidation was studied in acetate buffer as slightly acidic medium, and a role of acetate as bridging ligand between the two coppers, preorganizing the dinuclear center in a more catalytic efficient structure, could be established. The oxidation of β-naphthol and 3,5-ditertbutylphenol was studied as a model monophenolase reaction. The oxidation proceeds stoichiometrically, and the partial incorporation of 18O into β-naphthol when the reaction was performed using 18O2 suggests the existence of two competitive reaction pathways, a genuine monooxygenase mechanism and a radical pathway. However, the more challenging reaction on derivatives of l-/d-tyrosine did not lead to the desired monooxygenase product but only to products of radical oxidation. Complex [Cu2(mXHI)]4+ was also used for the catalytic sulfoxidation of thioanisole in the presence of hydroxylamine as cosubstrate, in a preliminary attempt to model the reaction of external monooxygenases. The reaction proceeds with 25 turnovers, but the enantiomeric excess of sulfoxide was modest.

Preparation method of N(pi)-methyl-L-histidine derivative and application thereof to synthesis of whale carnosine

The invention relates to a preparation method of an N(pi)-methyl-L-histidine derivative and a method for preparing anserine from the synthesized N(pi)-methyl-L-histidine derivative. By the preparationmethod, raw materials are cheap and easy to obtain, the selectivity is good and the yield is high; the operation is simple and easy to implement, a technology is stable, the control is easy, treatment after a reaction is convenient, the product yield is good, the purity is high, and the preparation method can be economically and conveniently applied to industrial production.