Pyridine → 2-(4-Fluorophenyl)-3-(2-methylsulfanyl-pyrimidin-4-yl)-3-oxo-propionic acid methyl ester

HRID 22662

反応式

HRID 22662 の反応式
N1C=CC=CC=1.[CH3:7][O:8][C:9](=[O:28])[CH:10]([C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=1)[CH:11]([C:13]1[CH:18]=[CH:17][N:16]=[C:15]([S:19][CH3:20])[N:14]=1)[OH:12]>C(Cl)Cl.CCOCC.[Cr]>[CH3:7][O:8][C:9](=[O:28])[CH:10]([C:21]1[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=1)[C:11]([C:13]1[CH:18]=[CH:17][N:16]=[C:15]([S:19][CH3:20])[N:14]=1)=[O:12]

参加物

6

反応物 2

HCID 1049PyridineHCID 129914022-(4-Fluorophenyl)-3-(2-methylsulfanyl-pyrimidin-4-yl)-3-hydroxypropionic acid methyl ester

生成物 1

HCID 129914032-(4-Fluorophenyl)-3-(2-methylsulfanyl-pyrimidin-4-yl)-3-oxo-propionic acid methyl ester収率 43%

試薬・触媒・溶媒 3

HCID 23976Chromium触媒HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a suspension of CrO3 in CH2Cl2 (300 mL) is added pyridine. The mixture is stirred vigorously for 1 hour at room temp. A solution of the crude 2-(4-fluorophenyl)-3-(2-methylsulfanyl-pyrimidin-4-yl)-3-hydroxypropionic acid methyl ester, 2, prepared above in CH2Cl2 (50 mL) is added dropwise to the chromium suspension. The reaction mixture is stirred at room temperature for 16 hours, diluted with ether (1 L) and filtered through a pad of Celite. The filtrate is concentrated in vacuo and the resulting residue is purified over silica (25% EtOAc/hexanes) to afford 3.7 g (43% yield) of the desired product as a yellow solid.

後処理

  1. stirringThe reaction mixture is stirred at room temperature for 16 hours
  2. filtrationfiltered through a pad of Celite
  3. concentrationThe filtrate is concentrated in vacuo
  4. customthe resulting residue is purified over silica (25% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-7097432dc3454a69a351135a03291a4a
出典データセット
uspto-grants-2005_02
特許番号
US06849627B2

関連ノート

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