Dimethylformamide → HCID 58269808, compound

HRID 1917093Notes

Reaction equation

HRID 1917093 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2C(=O)N[C:17](=O)[NH:18][CH:19]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].CI.CC[O:28]C(C)=O.[CH3:32][N:33]([CH3:36])[CH:34]=[O:35]>>[CH2:1]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[C:34](=[O:35])[N:33]([CH3:36])[C:32](=[O:28])[N:18]([CH3:17])[CH:19]=2)[CH2:12][CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 2814986HCID 2814986, compound

Product 1

HCID 58269808HCID 58269808, compound

Conditions

Temperature
0 °C

Procedure

9.6 g (33.53 mmol) of 5-(4-benzyl-piperazin-1-yl)-1H-pyrimidine-2,4-dione are placed at 0° C. in 10 mL of dimethylformamide. 2.95 g (73.56 mmol) of sodium hydride (at 60% in paraffin) are added portion wise. The mixture is stirred for 40 min at 0° C. 5 mL (80.5 mmol) of methyl iodide are added, the medium is stirred at room temperature for 7 h. After concentration of the reaction medium, the obtained residue is taken up with AcOEt and washed with water. After drying on MgSO4, the organic phase is concentrated. The obtained residue is triturated with ether, and then a precipitate is isolated by filtration. 4 g of intermediate 13a are obtained as a beige powder (yield: 38%).

Workup

  1. stirringthe medium is stirred at room temperature for 7 h
  2. washwashed with water
  3. customAfter drying on MgSO4
  4. concentrationthe organic phase is concentrated
  5. customThe obtained residue is triturated with ether
  6. customa precipitate is isolated by filtration

Sources & evidence

ORD record
ord-f9a3374e16c9491d91c0cc9074c1b3b8
Source dataset
uspto-grants-2013_12
Patent number
US08618287B2

Reaction notes

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