Dimethyl Sulfoxide → 6-methyl-5-(3-(2-(methylamino)pyrimidin-4-yl)pyridin-2-yloxy)isoquinolin-1(2H)-one

HRID 1668984Notes

Reaction equation

CS(C)=O.[OH:5][C:6]1[C:15]([CH3:16])=[CH:14][CH:13]=[C:12]2[C:7]=1[CH:8]=[CH:9][NH:10][C:11]2=[O:17].Cl[C:19]1[C:24]([C:25]2[CH:30]=[CH:29][N:28]=[C:27]([NH:31][CH3:32])[N:26]=2)=[CH:23][CH:22]=[CH:21][N:20]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O.CC(O)=O>[CH3:16][C:15]1[C:6]([O:5][C:19]2[C:24]([C:25]3[CH:30]=[CH:29][N:28]=[C:27]([NH:31][CH3:32])[N:26]=3)=[CH:23][CH:22]=[CH:21][N:20]=2)=[C:7]2[C:12](=[CH:13][CH:14]=1)[C:11](=[O:17])[NH:10][CH:9]=[CH:8]2

Participants

Conditions

Temperature: 130 °C

Procedure

DMSO (65 mL) was added to a vial containing 5-hydroxy-6-methylisoquinolin-1(2H)-one (5.50 g, 31.4 mmol) and 4-(2-chloropyridin-3-yl)-N-methylpyrimidin-2-amine (6.93 g, 31.4 mmol). Cesium carbonate (30.7 g, 94.2 mmol) was added to the vial, and the vial was sealed and heated to 130° C. for 16 hours. The vial was allowed to cool to ambient temperature and the mixture was diluted with water (˜1 L) and neutralized with AcOH. The precipitate was filtered to afford 6-methyl-5-(3-(2-(methylamino)pyrimidin-4-yl)pyridin-2-yloxy)isoquinolin-1(2H)-one. MS (M+H)+ 360.

Workup

customwas sealed
temperatureto cool to ambient temperature
filtrationThe precipitate was filtered

Sources & evidence

ORD record: ord-f7f5a185a3dc45448ac7105c091aef3d
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07989461B2

Reaction notes

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