Water → HCID 70338952, compound

HRID 1416129Notes

Reaction equation

HRID 1416129 reaction equation
[F:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]3[N:17]=[CH:16][C:15]([OH:18])=[CH:14][N:13]=3)[CH:10]=2)[CH:5]=[C:4]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[N:3]=1.[H-].[Na+].[CH2:30](Br)[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37].O>CN(C=O)C>[CH2:30]([O:18][C:15]1[CH:14]=[N:13][C:12]([C:9]2[CH:10]=[C:11]3[C:6]([CH:5]=[C:4]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[N:3]=[C:2]3[F:1])=[CH:7][CH:8]=2)=[N:17][CH:16]=1)[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]

Participants

6

Reactant 4

HCID 962WaterHCID 81401-BromooctaneHCID 24758Sodium hydrideHCID 538613662-[1-Fluoro-3-(octyloxy)isoquinolin-7-yl]pyrimidin-5-ol

Product 1

HCID 70338952HCID 70338952, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

10 mmol of 1-fluoro-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-fluoro-3-octyloxyisoquinoline. 1-Fluoro-7-(5-hydroxypyrimidin-2-yl)-3-alkyloxyisoquinolines can for example be reacted analogously to Example 3 with 2-fluoroalkyl sulfonates, 2,3-difluoroalkyl sulfonates, 3-alkyloxirane-2-methyl sulfonates, (ω-bromoalkyl)cyclopropanes or 1-bromodimethylsilanylalkanes.

Workup

  1. stirringthe mixture is stirred at 60° C. for a further 140 minutes
  2. extractionThe mixture is extracted with dichloromethane
  3. customthe combined organic phases are dried
  4. customthe solvent is removed in vacuo
  5. customthe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-46d16d2f5c6342aca292e851278ebd91
Source dataset
uspto-grants-1999_06
Patent number
US05911913

Reaction notes

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