Sodium hydride → 4-[2-[4-Methyl-2-propyl-6-oxo 1,6-dihydro-1-pyrimidinyl]ethoxy]benzaldehyde

HRID 1368081ノート

反応式

HRID 1368081 の反応式
[H-].[Na+].[CH3:3][C:4]1[N:5]=[C:6]([CH2:11][CH2:12][CH3:13])[NH:7][C:8](=[O:10])[CH:9]=1.[Li+].[Br-].Br[CH2:17][CH2:18][O:19][C:20]1[CH:27]=[CH:26][C:23]([CH:24]=[O:25])=[CH:22][CH:21]=1>CN(C=O)C.O>[CH3:3][C:4]1[N:5]=[C:6]([CH2:11][CH2:12][CH3:13])[N:7]([CH2:17][CH2:18][O:19][C:20]2[CH:27]=[CH:26][C:23]([CH:24]=[O:25])=[CH:22][CH:21]=2)[C:8](=[O:10])[CH:9]=1

参加物

7

反応物 4

HCID 24758Sodium hydrideHCID 82050Lithium BromideHCID 2627064-(2-Bromoethoxy)BenzaldehydeHCID 1355166076-methyl-2-propylpyrimidin-4(3H)-one

生成物 1

HCID 118227094-[2-[4-Methyl-2-propyl-6-oxo 1,6-dihydro-1-pyrimidinyl]ethoxy]benzaldehyde収率 31%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒3 回

実験手順

To a stirred suspension of NaH (570 mg, 22.57 mmol, 95%) in dry DMF (35 ml) at 25° C. was added a solution of 4-methyl-2-propyl-1,6-dihydro-6-pyrimidone (2.64 g, 17.36 mmol) in dry DMF. After the effervescence has ceased, anhydrous LiBr (3.51 g, 40.0 mmol) was added followed by 4-[2-bromoethoxy]benzaldehyde (4.37 g, 19.08 mmol) in dry DMF at the same temperature. The reaction mixture was immersed in a preheated oil bath at 70° C. and stirred for 2 h. The reaction mixture was cooled to room temperature, poured into water and extracted with EtOAc. The combined EtOAc layers were washed with brine, dried over anhydrous Na2SO4 and concentrated. The crude compound was chromatographed over silica gel using 3:7 EtOAc—pet. ether as eluent to obtain the title compound (1.61 g, 31%).

後処理

  1. customThe reaction mixture was immersed in a preheated oil bath at 70° C.
  2. extractionextracted with EtOAc
  3. washThe combined EtOAc layers were washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated
  6. customThe crude compound was chromatographed over silica gel using 3:7 EtOAc—pet. ether as eluent

出典と根拠

ORDレコード
ord-32699df006f34beebb53f056245a68d7
出典データセット
uspto-grants-2003_06
特許番号
US06573268B1

反応ノート

読み込み中…