Cesium fluoride → HCID 68326551, 화합물

HRID 631843노트

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HRID 631843 반응식
[CH2:1]([C:8]1[C:9](=[O:16])[NH:10][C:11](=[O:15])[NH:12][C:13]=1Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC1(C)C(C)(C)OB([C:25]2[CH2:30][CH2:29][CH:28]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH2:27][CH:26]=2)O1.[F-].[Cs+]>O1CCOCC1.O.[Cl-].[NH4+]>[CH2:1]([C:8]1[C:9](=[O:16])[NH:10][C:11](=[O:15])[NH:12][C:13]=1[C:34]1[CH2:35][CH2:36][CH:31]([C:28]2[CH:27]=[CH:26][CH:25]=[CH:30][CH:29]=2)[CH2:32][CH:33]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

7

반응물 3

HCID 25953Cesium fluorideHCID 112890924,4,5,5-Tetramethyl-2-(1,2,3,6-tetrahydro-[1,1'-biphenyl]-4-yl)-1,3,2-dioxaborolaneHCID 23648513HCID 23648513, 화합물

생성물 1

HCID 68326551HCID 68326551, 화합물수율 31.7%

시약·촉매·용매 3

HCID 962Water용매HCID 25517Ammonium Chloride용매HCID 312751,4-Dioxane용매

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온도
140 °C

실험 절차

A mixture of 5-benzyl-6-chloro-1H-pyrimidine-2,4-dione (WO006014394) (1.0 g), 4,4,5,5-tetramethyl-2-(4-phenylcyclohex-1-enyl)-[1,3,2]dioxaborolane (1.4 g), bis[di-tert-butyl(4-dimethylaminophenyl)phosphine]dichloropalladium(II) (0.06 g) and cesium fluoride (1.92 g) in 1,4-dioxane (18 mL) and water (2 mL) was heated at 140° C. in a microwave reactor for 20 minutes. The resulting mixture was diluted with saturated aqueous ammonium chloride and filtered to remove the precipitate. The filtrate was extracted with dichloromethane and the combined organic layers washed with water and brine, then dried over sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by column chromatography on silica gel, eluting with a mixture of methanol and dichloromethane (0:1 to 1:20 by volume) to afford the title compound 2a as an off-white solid (0.48 g). LCMS (Method A): Rt=3.56 min. (M+H)+=359. 1H NMR (DMSO-D6): δ 11.06 (1H, s), 10.69 (1H, s), 7.23-7.21 (10H, m), 5.84-5.79 (1H, m), 3.61 (2H, s), 3.57 (1H, s), 2.77-2.67 (1H, m), 2.19-2.16 (3H, m), 1.84-1.81 (1H, m), 1.68-1.67 (1H, m).

후처리

  1. filtrationfiltered
  2. customto remove the precipitate
  3. extractionThe filtrate was extracted with dichloromethane
  4. washthe combined organic layers washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by column chromatography on silica gel
  8. washeluting with a mixture of methanol and dichloromethane (0:1 to 1:20 by volume)

출처 및 근거

ORD 기록
ord-e3edab9a7f684295a0889f6e1ab4f621
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09321736B2

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