Water → 1,8-Difluoro-3-(octyloxy)-7-[5-(octyloxy)pyrimidin-2-yl]isoquinoline
Reaction equation
[F:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:13]3[N:18]=[CH:17][C:16]([OH:19])=[CH:15][N:14]=3)[C:10]=2[F:12])[CH:5]=[C:4]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[N:3]=1.[H-].[Na+].[CH2:31](Br)[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38].O>CN(C=O)C>[CH2:31]([O:19][C:16]1[CH:15]=[N:14][C:13]([C:9]2[C:10]([F:12])=[C:11]3[C:6]([CH:5]=[C:4]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[N:3]=[C:2]3[F:1])=[CH:7][CH:8]=2)=[N:18][CH:17]=1)[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38]Participants
6
Procedure
10 mmol of 1,8-difluoro-7-(5-hydroxypyrimidin-2-yl)-3-octyloxyisoquinoline are dissolved in 50 ml of DMF, and 11 mmol of sodium hydride are added. After the mixture has been stirred for 30 minutes, 11 mmol of 1 -octyl bromide are added dropwise, and the mixture is stirred at 60° C. for a further 140 minutes and poured into water. The mixture is extracted with dichloromethane, the combined organic phases are dried, the solvent is removed in vacuo, and the residue is chromatographed on silica gel, giving 9 mmol of 7-[5-(octyloxy)pyrimidin-2-yl]-1,8-difluoro-3-octyloxyisoquinoline.
Workup
- stirringthe mixture is stirred at 60° C. for a further 140 minutes
- extractionThe mixture is extracted with dichloromethane
- customthe combined organic phases are dried
- customthe solvent is removed in vacuo
- customthe residue is chromatographed on silica gel
Sources & evidence
- ORD record
- ord-1afe1779c14b4e58b1c4bc411ce2178b
- Source dataset
- uspto-grants-1999_03
- Patent number
- US05882546
Reaction notes
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