Sodium Carbonate → 6-(2-fluoropyridin-4-yl)-2,2-dimethyl-2,3-dihydrothieno[3,2-d]pyrimidin-4(1H)-one

HRID 2364009노트

반응식

HRID 2364009 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.[F:14][C:15]1[CH:20]=[C:19](B2OC(C)(C)C(C)(C)O2)[CH:18]=[CH:17][N:16]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1>[F:14][C:15]1[CH:20]=[C:19]([C:2]2[S:10][C:9]3[C:8](=[O:11])[NH:7][C:6]([CH3:13])([CH3:12])[NH:5][C:4]=3[CH:3]=2)[CH:18]=[CH:17][N:16]=1

참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 120601642-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 667434256-bromo-2,2-dimethyl-2,3-dihydrothieno[3,2-d]pyrimidin-4(1H)-one

생성물 1

HCID 667434126-(2-fluoropyridin-4-yl)-2,2-dimethyl-2,3-dihydrothieno[3,2-d]pyrimidin-4(1H)-one수율 69%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

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온도
70 °C

실험 절차

A mixture of 6-bromo-2,2-dimethyl-2,3-dihydrothieno[3,2-d]pyrimidin-4(1H)-one (0.052 g, 0.20 mmol), 2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (0.085 g, 0.60 mmol), 2 M sodium carbonate (0.30 mL, 0.60 mmol) and 1,1′-bis(diphenylphosphino)ferrocenepalladium (II) dichloride dichloromethane adduct (0.033 g, 0.040 mmol) in 1,4-dioxane (2 mL) was degassed with nitrogen and heated at 70° C. for 15 h. Then, the reaction was cooled to room temperature, and concentrated with silica gel (2 mL), and the residue was purified by flash chromatography (silica gel, ethyl acetate to 80:20 ethyl acetate/methanol) to give the title compound (0.038 g, 69%) as a yellow solid:

후처리

  1. customwas degassed with nitrogen
  2. temperatureThen, the reaction was cooled to room temperature
  3. concentrationconcentrated with silica gel (2 mL)
  4. customthe residue was purified by flash chromatography (silica gel, ethyl acetate to 80:20 ethyl acetate/methanol)

출처 및 근거

ORD 기록
ord-c4e725f8d6814af4a39884fc528f3038
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08691828B2

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