Water → HCID 69333344, compound

HRID 915062Notes

Reaction equation

[NH2:1][C:2]1[N:3]=[C:4]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:5]([C:13]2[CH:14]=[CH:15][C:16](=[O:22])[N:17]([CH:19]([CH3:21])[CH3:20])[N:18]=2)=[N:6][C:7]=1[C:8]1[CH:9]=[N:10][NH:11][CH:12]=1.[H-].[Na+].I[CH3:32].O>CC(C)=O>[NH2:1][C:2]1[N:3]=[C:4]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:5]([C:13]2[CH:14]=[CH:15][C:16](=[O:22])[N:17]([CH:19]([CH3:21])[CH3:20])[N:18]=2)=[N:6][C:7]=1[C:8]1[CH:9]=[N:10][N:11]([CH3:32])[CH:12]=1

Participants

Conditions

Temperature: 27.5 °C

Procedure

Under nitrogen atmosphere, 6-[5-amino-3-phenyl-6-(1H-pyrazol-4-yl)-2-pyrazinyl]-2-isopropyl-3(2H)-pyridazinone (120 mg) was added to a suspension of NaH (60% in oil) (14.2 mg) and the mixture was stirred at 25-30° C. for 30 minutes. The mixture was cooled in an ice bath and iodomethane (0.1 ml) was added. The mixture was stirred at the same time for 30 minutes and at 20-30° C. for one hour. After addition of water (3.6 ml), a precipitate was collected by filtration and purified by column chromatography on silica gel (EtOAc only) to give a solid. The solid was suspended in acetone and collected by filtration to give 6-[5-amino-6-(1-methyl-1H-pyrazol-4-yl)-3-phenyl-2-pyrazinyl]-2-isopropyl-3(2H)-pyridazinone (70 mg).

Workup

temperatureThe mixture was cooled in an ice bath
stirringThe mixture was stirred at the same time for 30 minutes and at 20-30° C. for one hour
filtrationa precipitate was collected by filtration
custompurified by column chromatography on silica gel (EtOAc only)
customto give a solid
filtrationcollected by filtration

Sources & evidence

ORD record: ord-c1908a943c3a45ee950509ec22665ea4
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07265120B2

Reaction notes

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