Potassium Carbonate → HCID 20061097, compound

HRID 1085293Notes

Reaction equation

HRID 1085293 reaction equation
Cl.[CH3:2][N:3]1[C:8]([NH:9][CH2:10][CH2:11][NH:12][CH2:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=2)=[CH:7][C:6](=[O:25])[N:5]([CH3:26])[C:4]1=[O:27].[C:28](=[O:31])([O-])[O-].[K+].[K+]>O>[CH3:2][N:3]1[C:8]([NH:9][CH2:10][CH2:11][N:12]([CH2:13][CH2:14][CH2:15][C:16]2[CH:17]=[CH:18][C:19]([N+:22]([O-:24])=[O:23])=[CH:20][CH:21]=2)[CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:31][CH3:28])=[CH:18][CH:17]=2)=[CH:7][C:6](=[O:25])[N:5]([CH3:26])[C:4]1=[O:27]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 20061225HCID 20061225, compound2×

Product 1

HCID 20061097HCID 20061097, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.4 g of 1,3-dimethyl-6-{2-[3-(4-nitrophenyl)propylamino]ethylamino}-2,4(1H,3H)-pyrimidinedione hydrochloride (Compound e) were dissolved in 5 ml of water, followed by the addition of potassium carbonate to render the solution alkaline. The solution was then extracted with chloroform. The thus-obtained chloroform solution was concentrated to dryness, followed by the addition of 0.6 g of p-methoxybenzyl bromide, 3 ml of triethylamine and 20 ml of isopropanol. The resultant mixture was heated for 8 hours under reflux. The solvent was distilled off under reduced pressure and the residue was directly subjected to chromatographic purification on a silica gel (eluent: chloroform/methanol=40/1, by volume), thereby obtaining 0.55 g of 1,3-dimethyl-6-{2-[N-(4-methoxybenzyl)-3-(4-nitrophenyl)propylamino]ethylamino}-2,4(1H,3H)-pyrimidinedione.

Workup

  1. extractionThe solution was then extracted with chloroform
  2. concentrationThe thus-obtained chloroform solution was concentrated to dryness
  3. additionfollowed by the addition of 0.6 g of p-methoxybenzyl bromide, 3 ml of triethylamine and 20 ml of isopropanol
  4. temperatureThe resultant mixture was heated for 8 hours
  5. temperatureunder reflux
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe residue was directly subjected to chromatographic purification on a silica gel (eluent: chloroform/methanol=40/1, by volume)

Sources & evidence

ORD record
ord-7a4b672abbba4236a1f384a8e52b4628
Source dataset
uspto-grants-1991_04
Patent number
US05008267

Reaction notes

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