Water → HCID 67977698, compound

HRID 1468790Notes

Reaction equation

HRID 1468790 reaction equation
[H-].[Na+].[CH2:3]([C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)[CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].Cl[C:17]1[N:18]([CH3:30])[C:19](=[O:29])[CH:20]=[C:21]([C:23]2[CH:28]=[CH:27][N:26]=[CH:25][N:24]=2)[N:22]=1.O>CN(C)C=O>[CH2:3]([C:9]1[CH:10]=[CH:11][C:12]([O:15][C:17]2[N:18]([CH3:30])[C:19](=[O:29])[CH:20]=[C:21]([C:23]3[CH:28]=[CH:27][N:26]=[CH:25][N:24]=3)[N:22]=2)=[CH:13][CH:14]=1)[CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

6

Reactant 4

HCID 962WaterHCID 171324-n-HexylphenolHCID 24758Sodium hydrideHCID 179544602-Chloro-3-methyl-6-(pyrimidin-4-YL)pyrimidin-4-one

Product 1

HCID 67977698HCID 67977698, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of sodium hydride (60 wt % in mineral oil, 202 mg, 5.05 mmol) in N,N-dimethylformamide (1.0 ml) was added 4-hexylphenol (899 mg, 5.04 mmol) at room temperature, and stirred for one hour. 2-Chloro-1-methyl-1H-[4,4′]bipyrimidinyl-6-one (935 mg, 4.20 mmol) was added to the solution. The mixture was stirred at room temperature overnight. The mixture was poured into water, and extracted with dichloromethane. The organic layer was washed with water (three times), dried over sodium sulfate, and concentrated in vacuo. The residue was purified by silica gel column chromatography (eluent; hexane/ethyl acetate=50/50) to afford 2-(4-hexylphenoxy)-1-methyl-1H-[4,4′]bipyrimidinyl-6-one as a colorless solid (1.14 g, 3.13 mmol, 75%).

Workup

  1. stirringThe mixture was stirred at room temperature overnight
  2. extractionextracted with dichloromethane
  3. washThe organic layer was washed with water (three times)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography (eluent; hexane/ethyl acetate=50/50)

Sources & evidence

ORD record
ord-f003c1998041419a9165807bd43d61a0
Source dataset
uspto-grants-2015_04
Patent number
US09006232B2

Reaction notes

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