Sodium hydride → 4-(5-Benzylpyrazol-3-yloxy)-6-methoxy-7-(3-morpholinopropoxy)quinazoline

HRID 855672노트

반응식

HRID 855672 반응식
[CH2:1]([C:8]1[CH2:12][C:11](=[O:13])[NH:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Cl[C:17]1[C:26]2[C:21](=[CH:22][C:23]([O:29][CH2:30][CH2:31][CH2:32][N:33]3[CH2:38][CH2:37][O:36][CH2:35][CH2:34]3)=[C:24]([O:27][CH3:28])[CH:25]=2)[N:20]=[CH:19][N:18]=1>CN(C=O)C.[Cl-].[NH4+]>[CH2:1]([C:8]1[NH:9][N:10]=[C:11]([O:13][C:17]2[C:26]3[C:21](=[CH:22][C:23]([O:29][CH2:30][CH2:31][CH2:32][N:33]4[CH2:34][CH2:35][O:36][CH2:37][CH2:38]4)=[C:24]([O:27][CH3:28])[CH:25]=3)[N:20]=[CH:19][N:18]=2)[CH:12]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 3

HCID 24758Sodium hydrideHCID 118239414-Chloro-6-methoxy-7-(3-morpholin-4-ylpropoxy)quinazolineHCID 220592713-benzyl-1H-pyrazol-5(4H)-one

생성물 1

HCID 179427484-(5-Benzylpyrazol-3-yloxy)-6-methoxy-7-(3-morpholinopropoxy)quinazoline수율 79%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 25517Ammonium Chloride용매

실험 절차

3-Benzyl-4,5-dihydro-1H-pyrazol-5-one (174 mg, 1 mmol), (J. Chem. Soc. Perk. Trans 1, 1980, 1618-1621), was added to a suspension of sodium hydride (40 mg, 1 mmol, prewashed with pentane) in DMF (3 ml) under nitrogen. After stirring for 30 minutes at ambient temperature, 4-chloro-6-methoxy-7-(3-morpholinopropoxy)quinazoline (135 mg, 0.4 mmol) was added and the mixture was heated at 80° C for 1 hour. After cooling, the mixture was diluted with saturated aqueous ammonium chloride solution and partitioned between ethyl acetate and water. The precipitate was collected by filtration, washed with water, followed by ethanol, ether and dried under vacuum to give 4-(5-benzylpyrazol-3-yloxy)-6-methoxy-7-(3-morpholinopropoxy)quinazoline (150 mg, 79%).

후처리

  1. temperaturethe mixture was heated at 80° C for 1 hour
  2. temperatureAfter cooling
  3. custompartitioned between ethyl acetate and water
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with water
  6. customdried under vacuum

출처 및 근거

ORD 기록
ord-861d09854a0c4fa9811eae4b0e2e2452
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07262201B1

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