Chloroacetone → 2,6-Dimethylimidazo[1,2-b]pyridazine

HRID 226023ノート

反応式

HRID 226023 の反応式
[NH2:1][C:2]1[N:3]=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=1.Cl[CH2:10][C:11](=O)[CH3:12].C([O-])(O)=O.[Na+]>CCO>[CH3:12][C:11]1[N:1]=[C:2]2[CH:7]=[CH:6][C:5]([CH3:8])=[N:4][N:3]2[CH:10]=1

参加物

5

反応物 3

HCID 6571ChloroacetoneHCID 877126-Methylpyridazin-3-amineHCID 516892Sodium Bicarbonate

生成物 1

HCID 218176672,6-Dimethylimidazo[1,2-b]pyridazine収率 51%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A solution of 3-amino-6-methyl-pyridazine (4.53 g, 41.58 mmol) in EtOH (60 mL) is treated with chloroacetone (3.5 mL, 43.66 mmol). The reaction is refluxed overnight. While it is hot, NaHCO3 (8.7 g, 103.9 mmol) is added in portions. The resulting mixture is refluxed for 2 h. It is cooled to rt and filtered through silical gel, washed with EtOAc, and concentrated. Purification of the crude material by chromatography gives the title compound (3.1 g, 21.11 mmol, 51%). 1H NMR (CDCl3): δ 2.49 (s, 3H), 2.55 (s, 3H), 6.84 (d, J=9.3 Hz, 1H), 7.64 (s, 1H), 7.70 (d, J=9.3 Hz, 1H) ppm. ES-MS (m/z): calcd for C8H9N3 (M+H)+: 148.2. found: 148.1.

後処理

  1. temperatureThe reaction is refluxed overnight
  2. temperatureThe resulting mixture is refluxed for 2 h
  3. filtrationfiltered through silical gel
  4. washwashed with EtOAc
  5. concentrationconcentrated
  6. customPurification of the crude material by chromatography

出典と根拠

ORDレコード
ord-d8c34bddadeb48b6a48b90880cda2565
出典データセット
uspto-grants-2009_07
特許番号
US07557103B2

反応ノート

読み込み中…