Thiophenol → HCID 66849112、化合物

HRID 1034593ノート

反応式

HRID 1034593 の反応式
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[NH2:10][C:11]1[C:16](Br)=[N:15][C:14]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)=[CH:13][N:12]=1>CN(C=O)C>[NH2:10][C:11]1[C:16]([S:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[N:15][C:14]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)=[CH:13][N:12]=1

参加物

5

反応物 3

HCID 7969ThiophenolHCID 24758Sodium hydrideHCID 715237102-Amino-3-bromo-5-(4-methoxyphenyl)pyrazine

生成物 1

HCID 66849112HCID 66849112、化合物収率 70%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
7.5 °C

実験手順

To a cooled solution of thiophenol (0.08 mL, 0.7 mmol) in dry DMF (10 mL), sodium hydride (NaH) (0.025 g, 1.00 mmol) was added and the resulting mixture was stirred for 15 min at 5-10° C. After this time 2-amino-3-bromo-5-(4-methoxyphenyl)pyrazine 17a (0.20 g, 0.71 mmol) was added and the mixture refluxed for 6 h, cooled and extracted with EtOAc. The organic layer was washed with water, dried over Na2SO4, filtered and the solvent removed under reduced pressure to get a crude that was purified by flash chromatography using petroleum ether-EtOAc (65:45 v/v) as eluent, to obtain 0.15 g of the title compound 18a as an orange solid (mp 89-90° C., 70% yield). 1H-NMR (CDCl3): 3.81 (s, 3H), 4.90 (br s, 2H), 6.89 (d, J=8.7, 2H), 7.33-7.39 (m, 7.45-7.50 (m, 2H), 7.69 (d, J=8.7, 2H), 8.28 (s, 1H). MS (ESI): m/z 310 (M+H+).

後処理

  1. temperaturethe mixture refluxed for 6 h
  2. temperaturecooled
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with water
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customthe solvent removed under reduced pressure
  8. customto get a crude that
  9. customwas purified by flash chromatography

出典と根拠

ORDレコード
ord-7b74cafae9034ef3bff415d84327c0b2
出典データセット
uspto-grants-2013_10
特許番号
US08546147B2

反応ノート

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