Potassium Carbonate → (Z)-2-(3-methoxy-4-(5-(2-methoxy-5-(3,4,5-trimethoxystyryl)phenoxy)pentyloxy)phenyl)-2,3-dihydroquinazolin-4(1H)-one

HRID 334323

反応式

HRID 334323 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[CH:10]\[C:11]2[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[C:13]([O:21][CH3:22])[CH:12]=2)=[CH:5][C:4]=1[OH:23].C(=O)([O-])[O-].[K+].[K+].Br[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][O:36][C:37]1[CH:42]=[CH:41][C:40]([CH:43]2[NH:52][C:51](=[O:53])[C:50]3[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=3)[NH:44]2)=[CH:39][C:38]=1[O:54][CH3:55]>CN(C=O)C.C(OCC)(=O)C.CCCCCC>[CH3:55][O:54][C:38]1[CH:39]=[C:40]([CH:43]2[NH:52][C:51](=[O:53])[C:50]3[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=3)[NH:44]2)[CH:41]=[CH:42][C:37]=1[O:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][O:23][C:4]1[CH:5]=[C:6](/[CH:9]=[CH:10]\[C:11]2[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[C:13]([O:21][CH3:22])[CH:12]=2)[CH:7]=[CH:8][C:3]=1[O:2][CH3:1]

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 5351344Combretastatin A4HCID 510425832-[4-(5-Bromo-pentyloxy)-3-methoxy-phenyl]-2,3-dihydro-1H-quinazolin-4-one

生成物 1

HCID 117687597(Z)-2-(3-methoxy-4-(5-(2-methoxy-5-(3,4,5-trimethoxystyryl)phenoxy)pentyloxy)phenyl)-2,3-dihydroquinazolin-4(1H)-one収率 83.4%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 21226206Ethyl acetate hexane溶媒

反応条件

温度
30 °C

実験手順

(Z)-2-methoxy-5-(3,4,5-trimethoxystyryl)phenol (38a) (316.35 mg 1.0 mmol) in DMF (20 mL) was added anhydrous potassium carbonate (690 mg, 5.0 mmol) and 2-[4-(5-Bromo-pentyloxy)-3-methoxy-phenyl]-2,3-dihydro-1H-quinazolin-4-one (2d) (419.29 mg, 1.0 mmol). The reaction mixture was stirred at a temperature of 30° C. for 30 h and the reaction was monitored by TLC using ethyl acetate-hexane (6:4) as a solvent system. Then to this ice is added and extracted with ethyl acetate. The solvent was evaporated under vacuum to afford the crude product. This was further purified by column chromatography using ethyl acetate:hexane (6:4) as a solvent system to obtain the pure product (39d) (546 mg, 80% yield).

後処理

  1. extractionextracted with ethyl acetate
  2. customThe solvent was evaporated under vacuum
  3. customto afford the crude product
  4. customThis was further purified by column chromatography

出典と根拠

ORDレコード
ord-c2f30562fb904be4acfb5368de4957b3
出典データセット
uspto-grants-2014_11
特許番号
US08883809B2

関連ノート

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