Dimethyl Sulfide → 6-{5-[(dimethyl-lambda~4~-sulfanylidene)amino]-3-phenyl-2-pyrazinyl}-2-isopropyl-3(2H)-pyridazinone

HRID 915049Notes

Reaction equation

[NH2:1][C:2]1[N:3]=[C:4]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:5]([C:8]2[CH:9]=[CH:10][C:11](=[O:17])[N:12]([CH:14]([CH3:16])[CH3:15])[N:13]=2)=[N:6][CH:7]=1.[CH3:24][S:25][CH3:26].ClN1C(=O)CCC1=O.C[O-].[Na+]>CO.O>[CH3:24][S:25](=[N:1][C:2]1[N:3]=[C:4]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:5]([C:8]2[CH:9]=[CH:10][C:11](=[O:17])[N:12]([CH:14]([CH3:16])[CH3:15])[N:13]=2)=[N:6][CH:7]=1)[CH3:26]

Participants

Conditions

Temperature: 22.5 °C

Procedure

To a suspension of 6-(5-amino-3-phenyl-2-pyrazinyl)-2-isopropyl-3(2H)-pyridazinone (1.01 g) was added dimethyl sulfide (0.263 ml) and N-chlorosuccinimide (435 mg) under −5° C. The mixture was stirred at −5° C. for 30 minutes and at 20-25° C. for 20 hours. A solution of 28% sodium methoxide in MeOH (1.13 ml) was added to the mixture and the solution was stirred at the same temperature for an hour. After addition of water (10 ml), the organic layer was collected, dried over MgSO4, concentrated under reduced pressure and purified by column chromatography on silica gel eluting with a mixture of MeOH and EtOAc (1:99 v/v) to give 6-{5-[(dimethyl-lambda˜4˜-sulfanylidene)amino]-3-phenyl-2-pyrazinyl}-2-isopropyl-3(2H)-pyridazinone as a solid (0.80 g).

Workup

stirringthe solution was stirred at the same temperature for an hour
customthe organic layer was collected
dry with materialdried over MgSO4
concentrationconcentrated under reduced pressure
custompurified by column chromatography on silica gel eluting with a mixture of MeOH and EtOAc (1:99 v/v)

Sources & evidence

ORD record: ord-3a3af26c3ff441169ea21a07f3e7a828
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07265120B2

Reaction notes

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