Potassium Carbonate → 4-(Pyrimidin-5-yloxy)benzaldehyde

HRID 1850173노트

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HRID 1850173 반응식
[N:1]1[CH:6]=[C:5]([OH:7])[CH:4]=[N:3][CH:2]=1.F[C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][CH:10]=1.CS([O-])=O.[Na+].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[N:1]1[CH:6]=[C:5]([O:7][C:9]2[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][CH:10]=2)[CH:4]=[N:3][CH:2]=1

참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 680234-FluorobenzaldehydeHCID 565855Pyrimidin-5-olHCID 2733271Sodium methanesulfinate

생성물 1

HCID 716702454-(Pyrimidin-5-yloxy)benzaldehyde수율 64%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

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온도
120 °C

실험 절차

To a solution of pyrimidin-5-ol (500 mg, 5.20 mmol) in DMF (5.20 mL) under argon was added 4-fluorobenzaldehyde (0.558 mL, 5.20 mmol), sodium methanesulfinate (133 mg, 1.30 mmol), and potassium carbonate (1.079 g, 7.81 mmol). The reaction mixture was heated at 120° C. for 3 hour. The mixture was allowed to cool to room temperature and was diluted with water (25 mL). The mixture was extracted with EtOAc (2×25 mL). The combined organic layers were washed with brine (2×50 mL), dried over sodium sulfate, filtered off and concentrated under reduced pressure. The residue was purified by column chromatography [SiO2, 24 g, heptane/ethyl acetate], providing 4-(pyrimidin-5-yloxy)benzaldehyde (666 mg) as a yellow solid. LCMS m/z 201.0 (M+H)+, Rt 0.52 min.

후처리

  1. temperatureto cool to room temperature
  2. extractionThe mixture was extracted with EtOAc (2×25 mL)
  3. washThe combined organic layers were washed with brine (2×50 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered off
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography [SiO2, 24 g, heptane/ethyl acetate]

출처 및 근거

ORD 기록
ord-16381282551042faa97d3bf02a4fd826
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08957068B2

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