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Sodium hydride → 4-Chloro-2-[(2,3-difluorophenyl)methylthio]-6-{(1R)-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]ethoxy}pyrimidine

HRID 1024905
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인쇄 미리보기

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HRID 1024905 반응식
[CH3:1][C:2]1([CH3:10])[O:6][C@@H:5]([C@H:7]([OH:9])[CH3:8])[CH2:4][O:3]1.[H-].[Na+].[Cl:13][C:14]1[CH:19]=[C:18](Cl)[N:17]=[C:16]([S:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[C:24]=2[F:30])[N:15]=1>C1COCC1>[Cl:13][C:14]1[CH:19]=[C:18]([O:9][C@@H:7]([C@H:5]2[CH2:4][O:3][C:2]([CH3:10])([CH3:1])[O:6]2)[CH3:8])[N:17]=[C:16]([S:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[C:24]=2[F:30])[N:15]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 12241285(1R)-1-[(4R)-2,2-Dimethyl-1,3-dioxolan-4-yl]ethanol2회HCID 859280374,6-Dichloro-2-((2,3-difluorobenzyl)thio)pyrimidine

생성물 1

HCID 866198804-Chloro-2-[(2,3-difluorophenyl)methylthio]-6-{(1R)-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]ethoxy}pyrimidine

시약·촉매·용매 1

HCID 8028Tetrahydrofuran
용매

실험 절차

To a solution of (1R)-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]ethanol (the product of step iv) (0.24 g) in dry THF (10 mL) at 0° C. was added in portions sodium hydride (91 mg as 60% dispersion in mineral oil) followed in portions by 4,6-dichloro-2-[(2,3-difluorobenzyl)thio]pyrimidine (the product of example 1 step ii) (0.50 g). The reaction mixture was stirred at room temperature for 48 h then quenched with saturated aqueous ammonium chloride (10 mL) and diluted with ethyl acetate. The layers were separated and the aqueous layer extracted with further ethyl acetate. The combined organic extracts were washed with brine, dried (MgSO4), filtered and evaporated. The residue was purified by column chromatography on silica gel using EtOAc/isohexane (1:19 to 1:9 gradient) as eluent to give the subtitle compound as a pale yellow solid. Yield: 0.42 g.

후처리

  1. customthen quenched with saturated aqueous ammonium chloride (10 mL)
  2. additiondiluted with ethyl acetate
  3. customThe layers were separated
  4. extractionthe aqueous layer extracted with further ethyl acetate
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by column chromatography on silica gel

출처 및 근거

ORD 기록
ord-7fc14a4255c0434fa00b79ba11f9893f
출처 데이터셋
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08722883B2

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