1,2-Dimethoxyethane → 4-(2,2-dimethyl-4-oxo-1,2,3,4-tetrahydrothieno[3,2-d]pyrimidin-6-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrazole-5-carbaldehyde

HRID 2364056노트

반응식

HRID 2364056 반응식
Br[C:2]1[S:10][C:9]2[C:8](=[O:11])[NH:7][C:6]([CH3:13])([CH3:12])[NH:5][C:4]=2[CH:3]=1.[CH:14]([C:16]1[N:20]([CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[N:19]=[CH:18][C:17]=1B(O)O)=[O:15].C(=O)([O-])[O-].[Cs+].[Cs+].COCCOC>O>[CH3:12][C:6]1([CH3:13])[NH:5][C:4]2[CH:3]=[C:2]([C:17]3[CH:18]=[N:19][N:20]([CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[C:16]=3[CH:14]=[O:15])[S:10][C:9]=2[C:8](=[O:11])[NH:7]1

참가 물질

6

반응물 4

HCID 80711,2-DimethoxyethaneHCID 10796Cesium carbonateHCID 667434256-bromo-2,2-dimethyl-2,3-dihydrothieno[3,2-d]pyrimidin-4(1H)-oneHCID 86662300(5-formyl-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrazol-4-yl)boronic acid

생성물 1

HCID 866623014-(2,2-dimethyl-4-oxo-1,2,3,4-tetrahydrothieno[3,2-d]pyrimidin-6-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrazole-5-carbaldehyde수율 54.1%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A mixture of 6-bromo-2,2-dimethyl-2,3-dihydrothieno[3,2-d]pyrimidin-4(1H)-one (0.444 g, 1.70 mmol), (5-formyl-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrazol-4-yl)boronic acid (0.554 g, 2.05 mmol), cesium carbonate (2.77 g, 8.50 mmol), 1,2-dimethoxyethane (15 mL) and water (4 mL) was purged with argon. Then, 1,1′-bis(diphenylphosphino)ferrocenepalladium (II) dichloride dichloromethane adduct (0.139 g, 0.17 mmol) was added, and the mixture was purged with argon again. The mixture was refluxed for 2 h. Then, the mixture was poured into water (100 mL) and EtOAc (100 mL). The insoluble materials were filtered off, and the organic layer was collected from the filtrate. This organic layer was washed with brine, dried over MgSO4 and concentrated under reduced pressure. The residual oil was purified by column chromatography (Purif, silica gel, 95:5 hexane/EtOAc to EtOAc) to afford the title compound (374 mg, 54%) as a yellow solid:

후처리

  1. customwas purged with argon
  2. customthe mixture was purged with argon again
  3. temperatureThe mixture was refluxed for 2 h
  4. additionThen, the mixture was poured into water (100 mL) and EtOAc (100 mL)
  5. filtrationThe insoluble materials were filtered off
  6. customthe organic layer was collected from the filtrate
  7. washThis organic layer was washed with brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated under reduced pressure
  10. customThe residual oil was purified by column chromatography (Purif, silica gel, 95:5 hexane/EtOAc to EtOAc)

출처 및 근거

ORD 기록
ord-5fef08eec0be4f89987ef205002a49ef
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08691828B2

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