Sodium hydride → HCID 67977677, compound

HRID 1468793Notes

Reaction equation

HRID 1468793 reaction equation
[H-].[Na+].[OH:3][CH2:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:6].Cl[C:14]1[N:15]([CH3:27])[C:16](=[O:26])[CH:17]=[C:18]([C:20]2[CH:25]=[CH:24][N:23]=[CH:22][N:21]=2)[N:19]=1>O1CCCC1>[CH3:27][N:15]1[C:16](=[O:26])[CH:17]=[C:18]([C:20]2[CH:25]=[CH:24][N:23]=[CH:22][N:21]=2)[N:19]=[C:14]1[O:3][CH2:4][C:5](=[O:6])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 68490alpha-HydroxyacetophenoneHCID 179544602-Chloro-3-methyl-6-(pyrimidin-4-YL)pyrimidin-4-one

Product 1

HCID 67977677HCID 67977677, compoundYield 5.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of sodium hydride (60 wt % in oil, 0.23 g, 6.3 mmol) in tetrahydrofuran (5 ml) was added 2-hydroxyacetophenone (0.92 g, 6.75 mmol) in tetrahydrofuran (5 ml) and the mixture was stirred at room temperature. After 30 minutes, 2-chloro-1-methyl-1H-[4,4′]bipyrimidinyl-6-one (1.0 g, 4.5 mmol) was added. The mixture was stirred under reflux for 8 hours. The mixture was cooled to room temperature and extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography (eluent; ethyl acetate) to afford 1-methyl-2-(2-oxo-2-phenyl-ethoxy)-1H-[4,4′]bipyrimidinyl-6-one (75 mg, 0.23 mmol, 5%) as a colorless solid.

Workup

  1. stirringThe mixture was stirred
  2. temperatureunder reflux for 8 hours
  3. temperatureThe mixture was cooled to room temperature
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography (eluent; ethyl acetate)

Sources & evidence

ORD record
ord-d6ef741eb6574f48b94619034c089490
Source dataset
uspto-grants-2015_04
Patent number
US09006232B2

Reaction notes

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