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

HRID 1351204ノート

反応式

HRID 1351204 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

反応条件

温度
90 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-1dc1d6917a6c416185049de7521a85b6
出典データセット
uspto-grants-2007_05
特許番号
US07217717B2

反応ノート

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