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Sodium hydride → HCID 86619878, 화합물

HRID 1024897
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HRID 1024897 반응식
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([S:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[C:12]=2[F:18])[N:3]=1.[OH:19][C@@H:20]1[CH2:24][O:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21]1.[H-].[Na+]>C1COCC1>[Cl:8][C:6]1[N:5]=[C:4]([S:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[C:12]=2[F:18])[N:3]=[C:2]([O:19][C@@H:20]2[CH2:24][O:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21]2)[CH:7]=1
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참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 7062393(R)-tert-butyl 5-hydroxyisoxazolidine-2-carboxylateHCID 859280374,6-Dichloro-2-((2,3-difluorobenzyl)thio)pyrimidine

생성물 1

HCID 86619878HCID 86619878, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
60 °C

실험 절차

To a stirred solution of 4,6-Dichloro-2-[(2,3-difluorobenzyl)thio]pyrimidine (the product of Example 1, step ii) (0.25 g) and 1,1-dimethylethyl (S)-4-hydroxyisoxazolidine-2-carboxylate (0.16 g) in dry THF (5 mL) was added 60% Sodium hydride (0.034 g) over 5 min. The reaction mixture was stirred and heated at 60° C. for 7 days, 1120 was added and the solvents were partially evaporated. The residue was extracted with EtOAc which was washed with H2O, dried (MgSO4) and the solvent evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel, eluting with Et2O/iso-hexane (1:9) to give the subtitle compound as a gum. Yield: 0.15 g.

후처리

  1. addition1120 was added
  2. customthe solvents were partially evaporated
  3. extractionThe residue was extracted with EtOAc which
  4. washwas washed with H2O
  5. dry with materialdried (MgSO4)
  6. customthe solvent evaporated under reduced pressure
  7. customThe residue was purified by flash chromatography on silica gel
  8. washeluting with Et2O/iso-hexane (1:9)

출처 및 근거

ORD 기록
ord-4edeab0830ab4368940e301535cf490a
출처 데이터셋
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08722883B2

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