Water → HCID 20061259, compound

HRID 1085270Notes

Reaction equation

HRID 1085270 reaction equation
Cl.[CH3:2][N:3]1[C:8]([N:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][O:18][C:19]3[CH:24]=[C:23]([N+:25]([O-:27])=[O:26])[CH:22]=[CH:21][C:20]=3[OH:28])[CH2:11][CH2:10]2)=[CH:7][C:6](=[O:29])[N:5]([CH3:30])[C:4]1=[O:31].[CH2:32](Br)[CH:33]=[CH2:34].C(=O)([O-])[O-].[K+].[K+].O>CC(C)=O>[CH3:2][N:3]1[C:8]([N:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][O:18][C:19]3[CH:24]=[C:23]([N+:25]([O-:27])=[O:26])[CH:22]=[CH:21][C:20]=3[O:28][CH2:34][CH:33]=[CH2:32])[CH2:11][CH2:10]2)=[CH:7][C:6](=[O:29])[N:5]([CH3:30])[C:4]1=[O:31]

Participants

6

Reactant 4

HCID 962WaterHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 20061074HCID 20061074, compound2×

Product 1

HCID 20061259HCID 20061259, compoundYield 77.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1 g of 1,3-dimethyl-6-{4-[3-(2-hydroxy-5-nitrophenyloxy)propyl]piperazin-1-yl}-2,4(1H,3H)-pyrimidinedione (Compound 145--free form), 0.31 g of allyl bromide and 0.36 g of potassium carbonate were suspended in 10 ml of dry acetone and heated under reflux for 5 hours. The reaction mixture was poured into 60 ml of water and then extracted three times with 30 ml portions of chloroform. The extract was washed first with a 0.5 N aqueous solution of sodium hydroxide and then with water. The chloroform solution was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by chromatography on a silica gel column (eluent: chloroform/methanol=20/1, by volume). The resulting oily substance was crystallized from ethanol, thereby obtaining 0.78 g of 1,3-dimethyl-6-{4-[3-(2-allyloxy-5-nitrophenyloxy)propyl]piperazin-1-yl}-2,4(1H,3H)-pyrimidinedione as crystals.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 5 hours
  3. extractionextracted three times with 30 ml portions of chloroform
  4. washThe extract was washed first with a 0.5 N aqueous solution of sodium hydroxide
  5. dry with materialThe chloroform solution was dried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe residue was purified by chromatography on a silica gel column (eluent: chloroform/methanol=20/1, by volume)
  8. customThe resulting oily substance was crystallized from ethanol

Sources & evidence

ORD record
ord-bc3745c931c54b25b19c48aab71ee9d5
Source dataset
uspto-grants-1991_04
Patent number
US05008267

Reaction notes

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