Sodium hydride → N1-Ethyl-5-(2-amino-4-pyrimidyl)oxy-1H-1-indolecarboxamide

HRID 2376814Notes

Reaction equation

HRID 2376814 reaction equation
[H-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][C:8]([O:12][C:13]3[CH:18]=[CH:17][N:16]=[C:15]([NH2:19])[N:14]=3)=[CH:9][CH:10]=2)[CH:5]=[CH:4]1.[CH2:20]([NH:22][C:23](=O)[O:24]C1C=CC=CC=1)[CH3:21]>CN(C)C=O>[CH2:20]([NH:22][C:23]([N:3]1[C:11]2[C:6](=[CH:7][C:8]([O:12][C:13]3[CH:18]=[CH:17][N:16]=[C:15]([NH2:19])[N:14]=3)=[CH:9][CH:10]=2)[CH:5]=[CH:4]1)=[O:24])[CH3:21]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 2802346phenyl N-ethylcarbamateHCID 219492624-(1H-5-indolyloxy)-2-pyrimidinamine

Product 1

HCID 21949217N1-Ethyl-5-(2-amino-4-pyrimidyl)oxy-1H-1-indolecarboxamideYield 63.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (157 mg, 3.93 mmol) was suspended in N,N-dimethylformamide (10 ml) under nitrogen atmosphere, and 4-(1H-5-indolyloxy)-2-pyrimidinamine (826 mg, 3.65 mmol) was gradually added while the reaction mixture was stirred at room temperature. After 10 minutes, the reaction mixture was cooled with an ice-water bath, phenyl N-ethylcarbamate (633 mg, 3.83 mmol) was added, the reaction mixture was heated to room temperature, and the solution was stirred for 4 hours. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with water and brine and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was purified by silica gel chromatography (eluent; ethyl acetate:hexane=3:1 to 4:1) to yield the title compound (691 mg, 2.32 mmol, 63.7%) as white powder.

Workup

  1. temperaturethe reaction mixture was cooled with an ice-water bath
  2. temperaturethe reaction mixture was heated to room temperature
  3. stirringthe solution was stirred for 4 hours
  4. customThe reaction mixture was partitioned between ethyl acetate and water
  5. washThe organic layer was washed with water and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThe solvent was distilled off
  8. customthe residue was purified by silica gel chromatography (eluent; ethyl acetate:hexane=3:1 to 4:1)

Sources & evidence

ORD record
ord-108e139cec394ac681782caefaa2af1e
Source dataset
uspto-grants-2008_12
Patent number
US07468380B2

Reaction notes

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