Sodium Carbonate → 3-(Pyrimidin-2-yl)benzaldehyde

HRID 50559

반응식

HRID 50559 반응식
C([O-])([O-])=O.[Na+].[Na+].[CH:7]([C:9]1[CH:10]=[C:11](B(O)O)[CH:12]=[CH:13][CH:14]=1)=[O:8].Br[C:19]1[N:24]=[CH:23][CH:22]=[CH:21][N:20]=1>O.COCCOC.ClCCl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[N:20]1[CH:21]=[CH:22][CH:23]=[N:24][C:19]=1[C:11]1[CH:10]=[C:9]([CH:14]=[CH:13][CH:12]=1)[CH:7]=[O:8]

참가 물질

8

반응물 3

HCID 10340Sodium CarbonateHCID 783452-BromopyrimidineHCID 27343563-Formylphenylboronic acid

생성물 1

HCID 226308183-(Pyrimidin-2-yl)benzaldehyde수율 63.3%

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 6344Dichloromethane용매HCID 80711,2-Dimethoxyethane용매

실험 절차

A mixture of Na2CO3 (4.74 g, 44.72 mmol) and 3-formylphenylboronic acid (3.40 g, 22.67 mmol) in water (15 mL) were added to a solution of 2-bromopyrimidine (3.00 g, 18.87 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.72 g, 0.62 mmol) in DME (30 mL) and the mixture was heated to reflux for 24 h. The cooled reaction mixture was diluted with dichloromethane, washed with sat. aq. NaHCO3 and brine, dried (MgSO4), and concentrated. Purification by chromatography (SiO2, 1:1 hexane/ethyl acetate) yielded 2.20 g (63%) of the title compound. MS 185 (M+H)+.

후처리

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 24 h
  3. customThe cooled reaction mixture
  4. washwashed with sat. aq. NaHCO3 and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customPurification by chromatography (SiO2, 1:1 hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-5076d7fc011144d69d550d838b5650a4
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06713455B2

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