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

HRID 50559

反応式

HRID 50559 の反応式
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]

参加物

8

反応物 3

HCID 10340Sodium CarbonateHCID 783452-BromopyrimidineHCID 27343563-Formylphenylboronic acid

生成物 1

HCID 226308183-(Pyrimidin-2-yl)benzaldehyde収率 63.3%

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-5076d7fc011144d69d550d838b5650a4
出典データセット
uspto-grants-2004_03
特許番号
US06713455B2

関連ノート

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