Sodium Carbonate → 5-(Pyrimidin-2-YL)thiophene-2-carbaldehyde

HRID 2416518노트

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HRID 2416518 반응식
C([O-])([O-])=O.[Na+].[Na+].[CH:7]([C:9]1[S:13][C:12](B(O)O)=[CH:11][CH:10]=1)=[O:8].Br[C:18]1[N:23]=[CH:22][CH:21]=[CH:20][N:19]=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:19]1[CH:20]=[CH:21][CH:22]=[N:23][C:18]=1[C:12]1[S:13][C:9]([CH:7]=[O:8])=[CH:10][CH:11]=1

참가 물질

8

반응물 3

HCID 10340Sodium CarbonateHCID 783452-BromopyrimidineHCID 27734305-Formyl-2-thiopheneboronic acid

생성물 1

HCID 226312225-(Pyrimidin-2-YL)thiophene-2-carbaldehyde수율 26%

시약·촉매·용매 4

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

실험 절차

A mixture of Na2CO3 (3.16 g) and 5-formyl-2-thiopheneboronic acid (2.4 g, 15.1 mmol) in water (15 mL) were added to a solution of 2-bromopyrimidine (2 g, 12.58 mmol) and tetrakis(triphenylphosphine)palladium(0) (480 mg, 0.46 mmol) in DME (30 mL) and the mixture was heated to reflux for 24 hr. 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 620 mg (26%) of the title compound. MS 191 (M+H)+.

후처리

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 24 hr
  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-2ccbb49f0c1a4c61aefa69f3b819d0d0
출처 데이터셋
uspto-grants-2004_11
특허 번호
US06825170B2

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