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

HRID 382270노트

반응식

HRID 382270 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매3회

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-389e9689614741f48a39d7e78fa76542
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06310069B1

반응 노트

불러오는 중…