Water → 6-[5-amino-6-(methylthio)-3-phenyl-2-pyrazinyl]-2-isopropyl-3(2H)-pyridazinone

HRID 915044Notes

Reaction equation

[NH2:1][C:2]1[N:3]=[C:4]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:5]([C:9]2[CH:10]=[CH:11][C:12](=[O:18])[N:13]([CH:15]([CH3:17])[CH3:16])[N:14]=2)=[N:6][C:7]=1Br.[CH3:25][S-:26].[Na+].O>CN1CCN(C)C1=O>[NH2:1][C:2]1[N:3]=[C:4]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:5]([C:9]2[CH:10]=[CH:11][C:12](=[O:18])[N:13]([CH:15]([CH3:17])[CH3:16])[N:14]=2)=[N:6][C:7]=1[S:26][CH3:25]

Participants

Conditions

Temperature: 102.5 °C

Procedure

A mixture of 6-(5-amino-6-bromo-3-phenyl-2-pyrazinyl)-2-isopropyl-3(2H)-pyridazinone (11.35 g) and sodium thiomethoxide (4.12 g) in 1,3-dimethyl-2-imidazolidinone (17 ml) was heated at 100-105° C. for one hour. The mixture was poured into water (170 ml). The precipitate was collected by filtration, dissolved in CHCl3, dried over MgSO4, concentrated under reduced pressure to give a residue. The residue was purified by column chromatography on silica gel eluting with a mixture of n-hexane and EtOAc (50:50 v/v) to give 6-[5-amino-6-(methylthio)-3-phenyl-2-pyrazinyl]-2-isopropyl-3(2H)-pyridazinone as a solid (4.32 g).

Workup

filtrationThe precipitate was collected by filtration
dissolutiondissolved in CHCl3
dry with materialdried over MgSO4
concentrationconcentrated under reduced pressure
customto give a residue
customThe residue was purified by column chromatography on silica gel eluting with a mixture of n-hexane and EtOAc (50:50 v/v)

Sources & evidence

ORD record: ord-05fdc35e946946c39311fc98c6517e56
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07265120B2

Reaction notes

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