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Methanol → 2-(2-(2-(2,5-Dichloropyrimidin-4-yl)ethyl)phenyl)propanamide

HRID 592415
ノート
印刷プレビュー

反応式

HRID 592415 の反応式
[Cl:1][C:2]1[N:7]=[C:6]([C:8]#[C:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH:16]([CH3:20])[C:17]([NH2:19])=[O:18])[C:5]([Cl:21])=[CH:4][N:3]=1.CO>CN(C=O)C.CCOC(C)=O.[Pt]=O>[Cl:1][C:2]1[N:7]=[C:6]([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH:16]([CH3:20])[C:17]([NH2:19])=[O:18])[C:5]([Cl:21])=[CH:4][N:3]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 2

HCID 887MethanolHCID 867123062-((2,5-Dichloropyrimidin-4-ylethynyl)phenyl)propanamide

生成物 1

HCID 867123072-(2-(2-(2,5-Dichloropyrimidin-4-yl)ethyl)phenyl)propanamide

試薬・触媒・溶媒 3

HCID 82844Platinum oxide (PtO)触媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate
溶媒

実験手順

A solution of 2-(2-((2,5-dichloropyrimidin-4-yl)ethynyl)phenyl)propanamide A29 (1.0 g, 3.1 mmol) in DMF (55 mL) and MeOH (5 mL) was stirred with platinum(II)oxide (0.21 g, 0.94 mmol) under an atmosphere of hydrogen for 120 hours at ambient temperature. The reaction mixture was diluted with EtOAc and filtered through a plug of Celite. The filter cake was washed with EtOAc and the solvents were removed in vacuo to give a crude residue that was purified by silica gel column chromatography (Combiflash Rf, 0-90% EtOAc in cyclohexane), giving the title compound A30 as an off white solid (0.65 g, 64%). LCMS-C: rt 4.98 min; m/z 324 [M+H]+.

後処理

  1. filtrationfiltered through a plug of Celite
  2. washThe filter cake was washed with EtOAc
  3. customthe solvents were removed in vacuo
  4. customto give a crude residue that
  5. customwas purified by silica gel column chromatography (Combiflash Rf, 0-90% EtOAc in cyclohexane)

出典と根拠

ORDレコード
ord-5b7962be32354250905e185ceb135078
出典データセット
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09238644B2

反応ノート

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