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

HRID 631376노트

반응식

HRID 631376 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
75 °C

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-fa9a52df1e4342068b5cb0d81d1b6abe
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09320739B2

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