501022-68-0

Basic information

• Product Name: 2(1H)-Pyrazinone, 6-(aminomethyl)-3,5-dimethyl- (9CI)
• Synonyms: 2(1H)-Pyrazinone, 6-(aminomethyl)-3,5-dimethyl- (9CI)
• CAS NO: 501022-68-0
• Molecular Formula: C7H11N3O
• Molecular Weight: 153.18174
• Product Categories: ALCOHOL
• Mol File: 501022-68-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2(1H)-Pyrazinone, 6-(aminomethyl)-3,5-dimethyl- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2(1H)-Pyrazinone, 6-(aminomethyl)-3,5-dimethyl- (9CI)(501022-68-0)
• EPA Substance Registry System: 2(1H)-Pyrazinone, 6-(aminomethyl)-3,5-dimethyl- (9CI)(501022-68-0)

Safety Data

• Hazardous Substances Data: 501022-68-0(Hazardous Substances Data)

Usage

Structure

A heterocyclic compound with a six-membered ring containing two nitrogen atoms and one oxygen atom.

Functional group

Contains an aminomethyl group, which is an amine bonded to a methylene group.

Substitution

Two methyl groups attached to the ring at positions 3 and 5.

Potential applications

Pharmaceutical, agrochemical, and materials science industries due to its unique structure and properties.

Upstream product

• 501022-66-8 6-benzyloxycarbonylaminomethyl-3,5-dimethyl-1,2-dihydropyrazine-2-one 
• 870537-69-2 Boc-2,3-diaminopropionic acid(Z)-[2,3-diaminopropionic acid(Z)]-CH₂Cl 
• 501022-57-7 3,6-bis(benzyloxycarbonylaminomethyl)-5-methyl-1,2-dihydropyrazin-2-one 

Downstream Products

• 57355-08-5 3,5,6-trimethyl-1,2-dihydropyrazin-2-one 

Relevant articles and documents

Studies on the mechanism of 1,2-dihydropyrazin-2-one ring formation from dipeptidyl chloromethyl ketone and its chemical properties: Immediate deamination during catalytic hydrogenation

1,2-Dihydropyrazin-2-one derivatives, which have two aminoalkyl groups at the positions 3 and 6, were found to be efficient tools for the construction of potent, selective and long-acting opioid mimetics. During the course of preparation, we found that the catalytic hydrogenation of 3,6- bis(benzyloxycarbonylaminomethyl)-5-methyl-1,2-dihydropyrazin-2-one to remove the benzyloxycarbonyl groups resulted in a side reaction. By MS and NMR studies and by preparation of additional 1,2-dihydropyrazin-2-one derivatives, the structure of the by-product was identified as 3-aminomethyl-5,6-dimethyl-1,2- dihydropyrazin-2-one. Preparation of additional compounds substituted with deuterium provided us with sufficient information to confirm the structure of the product and to support a cyclization mechanism in its formation.

Immediate deamination from the aminomethyl group attached to 1,2-dihydropyrazin-2-one derivative during catalytic hydrogenation

The catalytic hydrogenation of 3,6-bis(benzyloxycarbonylaminomethyl)-5-methyl-1,2-dihydropyrazin-2-one to remove benzyloxycarbonyl (Z) groups resulted in a side reaction. Purification by reverse-phase HPLC and analysis by proton nuclear magnetic resonance