5-Hydroxyindole → 5-(6-Amino-pyrimidin-4-yloxy)-1H-indole

HRID 2215495Notes

Reaction equation

HRID 2215495 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[CH:7]2.Cl[C:14]1[N:19]=[CH:18][N:17]=[C:16]([NH2:20])[CH:15]=1>CS(C)=O>[NH:9]1[C:10]2[C:6](=[CH:5][C:4]([O:3][C:14]3[N:19]=[CH:18][N:17]=[C:16]([NH2:20])[CH:15]=3)=[CH:12][CH:11]=2)[CH:7]=[CH:8]1

Participants

5

Reactant 3

HCID 160545-HydroxyindoleHCID 24758Sodium hydrideHCID 2380124-Amino-6-chloropyrimidine

Product 1

HCID 219492665-(6-Amino-pyrimidin-4-yloxy)-1H-indoleYield 59.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Sodium hydride (400 mg, 10.0 mmol) was suspended in dimethyl sulfoxide (20 ml) under nitrogen atmosphere, and 5-hydroxyindole (1.33 g, 10.0 mmol) was gradually added while the reaction mixture was stirred at room temperature. After 20 minutes, 6-chloropyrimidin-4-ylamine (1.04 g, 8.00 mmol) was added thereto, the reaction mixture was heated at 100° C. and stirred for 1 hour. After the reaction mixture was naturally cooled to room temperature, the reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with water and brine, and was dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was purified by silica gel column chromatography (eluent; ethyl acetate:hexane=3:1) to yield the title compound (1.07 g, 4.73 mmol, 59%) as a brown oil.

Workup

  1. temperaturethe reaction mixture was heated at 100° C.
  2. stirringstirred for 1 hour
  3. temperatureAfter the reaction mixture was naturally cooled to room temperature
  4. customthe reaction mixture was partitioned between ethyl acetate and water
  5. washThe organic layer was washed with water and brine
  6. dry with materialwas dried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off
  8. customthe residue was purified by silica gel column chromatography (eluent; ethyl acetate:hexane=3:1)

Sources & evidence

ORD record
ord-2a0ed14f5c284c39854670bfd138501d
Source dataset
uspto-grants-2006_09
Patent number
US07109219B2

Reaction notes

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