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Hydrogen Peroxide → 3-(3,4-dimethoxybenzyl)-6-(2-hydroxyethyl)-1-(tetrahydro-2H-pyran-4-yl)-quinazoline-2,4(1H,3H)-dione

HRID 1022509
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HRID 1022509 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:27]=[CH:28][C:29]=1[O:30][CH3:31])[CH2:6][N:7]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH:18]=[CH2:19])[CH:14]=2)[N:9]([CH:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)[C:8]1=[O:26].[OH-:32].[Na+].OO>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:27]=[CH:28][C:29]=1[O:30][CH3:31])[CH2:6][N:7]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH2:18][CH2:19][OH:32])[CH:14]=2)[N:9]([CH:20]2[CH2:21][CH2:22][O:23][CH2:24][CH2:25]2)[C:8]1=[O:26]
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HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 497631873-(3,4-dimethoxybenzyl)-6-ethenyl-1-(tetrahydro-2H-pyran-4-yl)quinazoline-2,4(1H,3H)-dione

생성물 1

HCID 497631863-(3,4-dimethoxybenzyl)-6-(2-hydroxyethyl)-1-(tetrahydro-2H-pyran-4-yl)-quinazoline-2,4(1H,3H)-dione

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

0.95 ml of a 1N solution of BH3-THF complex in THF is added, at 0° C., to a mixture of 0.1 g of 3-(3,4-dimethoxybenzyl)-6-ethenyl-1-(tetrahydro-2H-pyran-4-yl)quinazoline-2,4(1H,3H)-dione in 2 ml of THF. The reaction medium is allowed to warm to room temperature and is stirred for 1 hour. 2 ml of 1N sodium hydroxide and then 2 ml of 30% aqueous hydrogen peroxide solution are added. The resulting mixture is refluxed for 1 hour and then extracted with DCM. The organic phase is dried over Na2SO4, filtered and evaporated under reduced pressure. The residue is chromatographed on silica gel, eluting with a DCM/EtOAc mixture from (80/20, v/v) to (40/60) to give 0.057 g of the expected product.

후처리

  1. temperatureThe resulting mixture is refluxed for 1 hour
  2. extractionextracted with DCM
  3. dry with materialThe organic phase is dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe residue is chromatographed on silica gel
  7. washeluting with a DCM/EtOAc mixture from (80/20

출처 및 근거

ORD 기록
ord-949b954c0c464c88a146c329465fbd50
출처 데이터셋
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08722659B2

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