Allyl bromide → (6-Allyloxy-7-methoxy-quinazolin-4-yl)-(3-bromo-phenyl)-amine

HRID 1351204노트

반응식

HRID 1351204 반응식
[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:20][CH3:21])=[C:16]([OH:19])[CH:17]=3)[N:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1.C([O-])([O-])=O.[K+].[K+].[CH2:28](Br)[CH:29]=[CH2:30]>CC(C)=O>[CH2:30]([O:19][C:16]1[CH:17]=[C:18]2[C:13](=[CH:14][C:15]=1[O:20][CH3:21])[N:12]=[CH:11][N:10]=[C:9]2[NH:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=1)[CH:29]=[CH2:28]

참가 물질

5

반응물 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 103829564-(3-Bromoanilino)-6-hydroxy-7-methoxyquinazoline

생성물 1

HCID 21098400(6-Allyloxy-7-methoxy-quinazolin-4-yl)-(3-bromo-phenyl)-amine

시약·촉매·용매 1

HCID 180Acetone용매

반응 조건

온도
90 °C

실험 절차

To a solution of 4-(3-bromo-phenylamino)-7-methoxy-quinazolin-6-ol (1.24 g, 3.58 mmol) (from Example 17, Step B, supra) in acetone (250 mL) was added K2CO3 (0.99 g, 7.16 mmol), and allyl bromide (1.55 mL, 17.9 mmol) (Aldrich). The reaction mixture was heated with stirring at 90° C. for 4 hours. The mixture was cooled to room temperature, filtered and the filtrate was concentrated. The residue was purified by chromatography using EtOAc/CH2Cl2/Et3N (2:3:0.02) as eluent to give the desired (6-allyloxy-7-methoxy-quinazolin-4-yl)-(3-bromo-phenyl)-amine as a yellow oil. (Yield 0.55 g, 40%).

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureThe mixture was cooled to room temperature
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by chromatography

출처 및 근거

ORD 기록
ord-1dc1d6917a6c416185049de7521a85b6
출처 데이터셋
uspto-grants-2007_05
특허 번호
US07217717B2

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