Cesium carbonate → 3-(6-(Benzyloxy)-7-methoxyquinazolin-4-yloxy)aniline

HRID 871421ノート

反応式

HRID 871421 の反応式
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][C:18]=1[O:19][CH3:20])[N:15]=[CH:14][N:13]=[C:12]2Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:22][C:23]1[CH:24]=[C:25]([OH:29])[CH:26]=[CH:27][CH:28]=1.C([O-])([O-])=O.[Cs+].[Cs+]>C1COCC1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][C:18]=1[O:19][CH3:20])[N:15]=[CH:14][N:13]=[C:12]2[O:29][C:25]1[CH:24]=[C:23]([CH:28]=[CH:27][CH:26]=1)[NH2:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 115683-AminophenolHCID 114265806-(Benzyloxy)-4-chloro-7-methoxyquinazoline

生成物 1

HCID 668775223-(6-(Benzyloxy)-7-methoxyquinazolin-4-yloxy)aniline収率 90.8%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
75 °C

実験手順

To a solution of 6-(benzyloxy)-4-chloro-7-methoxyquinazoline (3.3 g, 0.01097 mol) and 3-aminophenol (1.2 g, 0.01097 mol) in THF (70 mL), Cs2CO3 (5.36 g, 0.0164 mol) was added at room temperature. The reaction mixture was stirred at 75° C. for 25 hr. The mixture was filtered and the solid was washed with ethyl acetate (100 mL). The organic phase was washed with water, brine and dried over MgSO4. The solvent was evaporated under vacuum and the solid was triturated with ethyl ether (20 mL). The solid was filtered and washed with ethyl ether to afford 3-(6-(benzyloxy)-7-methoxyquinazolin-4-yloxy)aniline (3.72 g, 90% yield). 1HNMR (DMSO-d6): δ 8.55 (s, 1H), 7.66 (s, 1H), 7.46 (m, 8H), 7.08 (t, 1H), 6.49 (d, 1H), 6.40 (m, 2H), 5.30 (s, 2H), 4.02 (s, 3H). LC-MS (ESI) m/z 508 (M+H)+.

後処理

  1. filtrationThe mixture was filtered
  2. washthe solid was washed with ethyl acetate (100 mL)
  3. washThe organic phase was washed with water, brine
  4. dry with materialdried over MgSO4
  5. customThe solvent was evaporated under vacuum
  6. customthe solid was triturated with ethyl ether (20 mL)
  7. filtrationThe solid was filtered
  8. washwashed with ethyl ether

出典と根拠

ORDレコード
ord-78f757cc539d41689db4db1468813c52
出典データセット
uspto-grants-2015_03
特許番号
US08969587B2

反応ノート

読み込み中…