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Tributylphosphine → 6-(2,2-difluoroethoxy)-3-(3,4-dimethoxybenzyl)-7-fluoro-1-(tetrahydro-2H-pyran-4-yl)-quinazoline-2,4(1H,3H)-dione

HRID 1022488
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HRID 1022488 반응식
[F:1][C:2]([F:5])(O)[CH3:3].C(P(CCCC)CCCC)CCC.CC(OC(/N=N/C(OC(C)C)=O)=O)C.[CH3:33][O:34][C:35]1[CH:36]=[C:37]([CH:59]=[CH:60][C:61]=1[O:62][CH3:63])[CH2:38][N:39]1[C:48](=[O:49])[C:47]2[C:42](=[CH:43][C:44]([F:51])=[C:45]([OH:50])[CH:46]=2)[N:41]([CH:52]2[CH2:57][CH2:56][O:55][CH2:54][CH2:53]2)[C:40]1=[O:58]>C1COCC1>[F:1][CH:2]([F:5])[CH2:3][O:50][C:45]1[CH:46]=[C:47]2[C:42](=[CH:43][C:44]=1[F:51])[N:41]([CH:52]1[CH2:57][CH2:56][O:55][CH2:54][CH2:53]1)[C:40](=[O:58])[N:39]([CH2:38][C:37]1[CH:59]=[CH:60][C:61]([O:62][CH3:63])=[C:35]([O:34][CH3:33])[CH:36]=1)[C:48]2=[O:49]
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참가 물질

6

반응물 4

HCID 13831TributylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 20243757DifluoroethanolHCID 497649193-(3,4-dimethoxybenzyl)-7-fluoro-6-hydroxy-1-(tetrahydro-2H-pyran-4-yl)quinazoline-2,4(1H,3H)-dione

생성물 1

HCID 497649206-(2,2-difluoroethoxy)-3-(3,4-dimethoxybenzyl)-7-fluoro-1-(tetrahydro-2H-pyran-4-yl)-quinazoline-2,4(1H,3H)-dione수율 82.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

0.125 g of difluoroethanol, 0.47 g of tributylphosphine and 0.38 g of DIAD are successively added to a solution of 0.4 g of the compound obtained in Step 4.7 in 15 ml of THF. This mixture is stirred overnight at room temperature. The reaction medium is evaporated under reduced pressure. The residue is chromatographed on silica gel, eluting with a PE/EtOAc mixture from (100/0, v/v) to (30/70) to give 0.38 g of the expected product.

후처리

  1. customThe reaction medium is evaporated under reduced pressure
  2. customThe residue is chromatographed on silica gel
  3. washeluting with a PE/EtOAc mixture from (100/0

출처 및 근거

ORD 기록
ord-0a265e92edec47c5bf256017413e63b2
출처 데이터셋
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08722659B2

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