Dimethylformamide → 4'-{[6-cyclopropyl-3-[2-(4-fluoro-2-methoxyphenyl)-2-oxoethyl]-2,4-dioxo-3,4-dihydrothieno[2,3-d]pyrimidin-1(2H)-yl]methyl}-3'-fluorobiphenyl-2-carbonitrile

HRID 1889380노트

반응식

HRID 1889380 반응식
[CH:1]1([C:4]2[S:30][C:7]3[N:8]([CH2:14][C:15]4[CH:20]=[CH:19][C:18]([C:21]5[C:22]([C:27]#[N:28])=[CH:23][CH:24]=[CH:25][CH:26]=5)=[CH:17][C:16]=4[F:29])[C:9](=[O:13])[NH:10][C:11](=[O:12])[C:6]=3[CH:5]=2)[CH2:3][CH2:2]1.Br[CH2:32][C:33]([C:35]1[CH:40]=[CH:39][C:38]([F:41])=[CH:37][C:36]=1[O:42][CH3:43])=[O:34].CN(C)C=O.[H-].[Na+]>C(OCC)(=O)C>[CH:1]1([C:4]2[S:30][C:7]3[N:8]([CH2:14][C:15]4[CH:20]=[CH:19][C:18]([C:21]5[C:22]([C:27]#[N:28])=[CH:23][CH:24]=[CH:25][CH:26]=5)=[CH:17][C:16]=4[F:29])[C:9](=[O:13])[N:10]([CH2:32][C:33]([C:35]4[CH:40]=[CH:39][C:38]([F:41])=[CH:37][C:36]=4[O:42][CH3:43])=[O:34])[C:11](=[O:12])[C:6]=3[CH:5]=2)[CH2:3][CH2:2]1

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 219784112-Bromo-1-(4-fluoro-2-methoxyphenyl)ethanoneHCID 593515214'-[(6-cyclopropyl-2,4-dioxo-3,4-dihydrothieno[2,3-d]pyrimidin-1(2H)-yl)methyl]-3'-fluorobiphenyl-2-carbonitrile

생성물 1

HCID 593515894'-{[6-cyclopropyl-3-[2-(4-fluoro-2-methoxyphenyl)-2-oxoethyl]-2,4-dioxo-3,4-dihydrothieno[2,3-d]pyrimidin-1(2H)-yl]methyl}-3'-fluorobiphenyl-2-carbonitrile수율 67.1%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

To a mixture of 4′-[(6-cyclopropyl-2,4-dioxo-3,4-dihydrothieno[2,3-d]pyrimidin-1(2H)-yl)methyl]-3′-fluorobiphenyl-2-carbonitrile (0.32 g), 2-bromo-1-(4-fluoro-2-methoxyphenyl)ethanone (0.25 g) and N,N-dimethylformamide (15 mL) was added 60% sodium hydride (0.046 g), and the mixture was stirred at room temperature for 2 hr. The reaction mixture was diluted with ethyl acetate, washed with 5% potassium hydrogensulfate and then saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the title compound as a colorless amorphous solid (0.3 g, 67%).

후처리

  1. washwashed with 5% potassium hydrogensulfate
  2. dry with materialsaturated brine, and dried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-751287af8ab34c9c8a542e2f76913202
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08501750B2

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