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Sodium hydride → 7-Benzyloxy-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one

HRID 1386317
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HRID 1386317 반응식
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13](=[O:19])[NH:14][CH:15]=[N:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[C:22]([O:28][CH2:29]Cl)(=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24]>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13](=[O:19])[N:14]([CH2:29][O:28][C:22](=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24])[CH:15]=[N:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 87885Chloromethyl pivalateHCID 1357631107-(Benzyloxy)-3,4-dihydroquinazolin-4-one

생성물 1

HCID 216992627-Benzyloxy-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one수율 92%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
7.5 °C

실험 절차

7-Benzyloxy-3,4-dihydroquinazolin-4-one (7.0 g, 27 mmol) was suspended in dry DMF (50 ml) and cooled to 5-10° C., then sodium hydride was added (1.22 g of a 60% suspension in mineral oil, 30 mmol). The reaction mixture was allowed to return to ambient temperature and chloromethyl pivalate (4.75 g, 31.5 mmol) was added over 10 minutes and the mixture stirred for 1 hour. The reaction mixture was quenched with water (250 ml), the aqueous phase adjusted to pH5 and extracted with ether (300 ml×3). The combined ether phases were washed with brine, dried (MgSO4) and the solvent removed by evaporation. The solid residue was triturated with isohexane, collected by filtration and dried under vacuum to give 7-benzyloxy-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one (9.1 g, 90%).

후처리

  1. customto return to ambient temperature
  2. customThe reaction mixture was quenched with water (250 ml)
  3. extractionextracted with ether (300 ml×3)
  4. washThe combined ether phases were washed with brine
  5. dry with materialdried (MgSO4)
  6. customthe solvent removed by evaporation
  7. customThe solid residue was triturated with isohexane
  8. filtrationcollected by filtration
  9. customdried under vacuum

출처 및 근거

ORD 기록
ord-5591ae9228df46d9ad635c504bed57fe
출처 데이터셋
uspto-grants-2001_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06265411B1

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