N-bromobutanimide → 5-Bromo-3-(5-tert-butyl-1,3,4-oxadiazol-2-yl)pyrazin-2-amine

HRID 1749668ノート

反応式

HRID 1749668 の反応式
[Br:1]N1C(=O)CCC1=O.[C:9]([C:13]1[O:17][C:16]([C:18]2[C:19]([NH2:24])=[N:20][CH:21]=[CH:22][N:23]=2)=[N:15][N:14]=1)([CH3:12])([CH3:11])[CH3:10]>C1COCC1>[Br:1][C:22]1[N:23]=[C:18]([C:16]2[O:17][C:13]([C:9]([CH3:12])([CH3:10])[CH3:11])=[N:14][N:15]=2)[C:19]([NH2:24])=[N:20][CH:21]=1

参加物

4

反応物 2

HCID 67184N-bromobutanimideHCID 867276543-(5-Tert-butyl-1,3,4-oxadiazol-2-yl)pyrazin-2-amine

生成物 1

HCID 867276555-Bromo-3-(5-tert-butyl-1,3,4-oxadiazol-2-yl)pyrazin-2-amine収率 90.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

1-Bromopyrrolidine-2,5-dione (18.57 g, 104.36 mmol) was added portionwise to a solution of 3-(5-tert-butyl-1,3,4-oxadiazol-2-yl)pyrazin-2-amine (20.8 g, 94.87 mmol) in THF (320 mL) and the solution was stirred at room temperature for 16 hours. The reaction mixture was concentrated and the residue was dissolved in dichloromethane (300 mL), washed with water (2×150 mL), brine, dried over magnesium sulfate and concentrated. The solvent was evaporated and the crude product was purified by flash chromatography on silica gel, eluting with 0 to 10% ethyl acetate in dichloromethane. The solvent was evaporated to dryness to afford 5-bromo-3-(5-tert-butyl-1,3,4-oxadiazol-2-yl)pyrazin-2-amine (25.5 g, 90%) as a beige solid: 1H NMR Spectrum; (CDCl3) 1.52 (9H, s), 8.23 (1H, s); Mass Spectrum [M+H]+=300.

後処理

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe residue was dissolved in dichloromethane (300 mL)
  3. washwashed with water (2×150 mL), brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe solvent was evaporated
  7. customthe crude product was purified by flash chromatography on silica gel
  8. washeluting with 0 to 10% ethyl acetate in dichloromethane
  9. customThe solvent was evaporated to dryness

出典と根拠

ORDレコード
ord-a2a00dff89354347b1e5b420963b914a
出典データセット
uspto-grants-2015_10
特許番号
US09156831B2

反応ノート

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