Sodium hydride → 5-bromo-1-(3-fluoro-benzyl)-3-methyl-3,4-dihydro-1H-quinazolin-2-one

HRID 459792ノート

反応式

HRID 459792 の反応式
[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][N:5]([CH3:13])[C:6](=[O:12])[NH:7]2.[H-].[Na+].[F:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH2:20]Br>>[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][N:5]([CH3:13])[C:6](=[O:12])[N:7]2[CH2:20][C:19]1[CH:22]=[CH:23][CH:24]=[C:17]([F:16])[CH:18]=1

参加物

4

反応物 3

HCID 24758Sodium hydrideHCID 680073-Fluorobenzyl bromideHCID 184445245-Bromo-3,4-dihydro-3-methylquinazolin-2(1H)-one

生成物 1

HCID 184445195-bromo-1-(3-fluoro-benzyl)-3-methyl-3,4-dihydro-1H-quinazolin-2-one収率 81.2%

反応条件

温度
0 °C

実験手順

To a solution of 5-bromo-3-methyl-3,4-dihydro-1H-quinazolin-2-one (132 mg, 0.55 mmol) in 5 ml anhydrous dimethylformanide was added sodium hydride (33 mg of a 60% suspension in mineral oil, 0.83 mmol) portionwise at 0° C. The solution was stirred with a magnetic stirrer at 0° C. for 20 minutes, at which time the initial offgassing ended. 3-Fluorobenzyl bromide (0.08 ml, 0.65 mmol) was added in one portion and the reaction mixture was stirred at 0° C. for an hour. The solution was allowed to warm to room temperature and the reaction mixture was partitioned between water and ethyl acetate. The aqueous layer was extracted with ethyl acetate and the combined organic fractions were washed with water and brine. After drying over MgSO4, the organic fraction was concentrated in vacuo and resulting residue was purified by flash chromatography to give 156 mg of 5-bromo-1-(3-fluoro-benzyl)-3-methyl-3,4-dihydro-1H-quinazolin-2-one as a yellow solid (81%). MS: 349.1 (M+H)+.

後処理

  1. stirringthe reaction mixture was stirred at 0° C. for an hour
  2. temperatureto warm to room temperature
  3. customthe reaction mixture was partitioned between water and ethyl acetate
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. washthe combined organic fractions were washed with water and brine
  6. dry with materialAfter drying over MgSO4
  7. concentrationthe organic fraction was concentrated in vacuo
  8. customresulting residue
  9. customwas purified by flash chromatography

出典と根拠

ORDレコード
ord-16e2bd3c6c7d451fbc9077204434e750
出典データセット
uspto-grants-2007_03
特許番号
US07196087B2

反応ノート

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