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Aluminium lithium hydride → 5-bromo-1-(2,6-dichlorophenyl)-7-(hydroxymethyl)-3-(4-methoxybenzyl)-3,4-dihydroquinazolin-2(1H)-one

HRID 394107
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HRID 394107 반응식
[Br:1][C:2]1[CH:11]=[C:10]([C:12](OC)=[O:13])[CH:9]=[C:8]2[C:3]=1[CH2:4][N:5]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=1)[C:6](=[O:24])[N:7]2[C:16]1[C:21]([Cl:22])=[CH:20][CH:19]=[CH:18][C:17]=1[Cl:23].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[Br:1][C:2]1[CH:11]=[C:10]([CH2:12][OH:13])[CH:9]=[C:8]2[C:3]=1[CH2:4][N:5]([CH2:25][C:26]1[CH:27]=[CH:28][C:29]([O:32][CH3:33])=[CH:30][CH:31]=1)[C:6](=[O:24])[N:7]2[C:16]1[C:17]([Cl:23])=[CH:18][CH:19]=[CH:20][C:21]=1[Cl:22]
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HCID 21226445Aluminium lithium hydrideHCID 22647942Methyl 5-bromo-1-(2,6-dichlorophenyl)-3-(4-methoxybenzyl)-2-oxo-1,2,3,4-tetrahydroquinazoline-7-carboxylate2회

생성물 1

HCID 226479525-bromo-1-(2,6-dichlorophenyl)-7-(hydroxymethyl)-3-(4-methoxybenzyl)-3,4-dihydroquinazolin-2(1H)-one

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

To a solution of methyl 5-bromo-1-(2,6-dichlorophenyl)-3-(4-methoxybenzyl)-2-oxo-1,2,3,4-tetrahydroquinazoline-7-carboxylate (INTERMEDIATE 27)(2 g, 3.63 mmol) in anhydrous THF at 0° C. was added lithium aluminum hydride (1.0M in THF, 4.7 mL, 4.73 mmol) slowly. The reaction was stirred at 0° C. for 40 min, quenched with water slowly and diluted with methylene chloride. The mixture was filtered through celite and rinsed with methylene chloride. Removal of the solvent and subsequent purification by flash chromatography using 20% of acetone in hexane as eluent provided the 5-bromo-1-(2,6-dichlorophenyl)-7-(hydroxymethyl)-3-(4-methoxybenzyl)-3,4-dihydroquinazolin-2(1H)-one as a white solid. 1H NMR (CDCl3, 500 MHz): δ 3.83 (s, 3H), 4.49 (s, 2H), 4.50 (s, 2H), 4.69 (s, 2H), 5.98 (s, 1H), 6.92 (d, 2H, J=8.5 Hz), 7.23 (s, 1H), 7.36 (m, 3H), 7.52 (d, 2H, J=8.0 Hz). MS (API-ES+): 523 (M+H).

후처리

  1. customquenched with water slowly
  2. additiondiluted with methylene chloride
  3. filtrationThe mixture was filtered through celite
  4. washrinsed with methylene chloride
  5. customRemoval of the solvent and subsequent purification by flash chromatography

출처 및 근거

ORD 기록
ord-472402837b2547e797c45c7046c8c418
출처 데이터셋
uspto-grants-2004_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06809199B2

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