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

HRID 2215492ノート

反応式

HRID 2215492 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-10f1423a9bf5462699d768f888d01125
出典データセット
uspto-grants-2006_09
特許番号
US07109219B2

反応ノート

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