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

HRID 1837293Notes

Reaction equation

HRID 1837293 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent3×

Procedure

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, 19.03 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%).

Workup

  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

Sources & evidence

ORD record
ord-fd787cc53de34be2abbb845b9d0eb289
Source dataset
uspto-grants-2004_08
Patent number
US06780992B2

Reaction notes

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