Water → 1,3-dimethyl-6-[4-(3-hydroxy-2-phenylpropyl)piperazin-1-yl]-2,4(1H,3H)-pyrimidinedione

HRID 1032968Notes

Reaction equation

HRID 1032968 reaction equation
[CH3:1][N:2]1[C:7]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH:15]([C:22](OCC)=[O:23])[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:10][CH2:9]2)=[CH:6][C:5](=[O:27])[N:4]([CH3:28])[C:3]1=[O:29].[H-].[Li+].[Al+3].[H-].[H-].[H-].O.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[CH3:1][N:2]1[C:7]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:22][OH:23])[CH2:10][CH2:9]2)=[CH:6][C:5](=[O:27])[N:4]([CH3:28])[C:3]1=[O:29]

Participants

6

Reactant 4

HCID 962WaterHCID 24436Sodium SulfateHCID 190270851,3-dimethyl-6-[4-(2-ethoxycarbonyl-2-phenylethyl)piperazin-1-yl]-2,4(1H,3H)-pyrimidinedioneHCID 21226445Aluminium lithium hydride

Product 1

HCID 190270991,3-dimethyl-6-[4-(3-hydroxy-2-phenylpropyl)piperazin-1-yl]-2,4(1H,3H)-pyrimidinedioneYield 43%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

1.3 g of 1,3-dimethyl-6-[4-(2-ethoxycarbonyl-2-phenylethyl)piperazin-1-yl]-2,4(1H,3H)-pyrimidinedione obtained in Example 4 was dissolved in 50 ml of tetrahydrofuran, and while the resulting solution was cooled to -20° C., 1.1 g of aluminum lithium hydride was divided into several portions and then added thereto separately. After stirring at -10° C. for 1 hour, 0.7 ml of water was added to the solution at the same temperature. The reaction solution was stirred for 2 or 3 hours, and 3 g of anhydrous sodium sulfate was added thereto, followed by allowing the solution to stand overnight. Afterward, insolubles were removed from the solution by filtration, and the filtrate was concentrated and the resulting residue was then dissolved in ethyl acetate. The obtained solution was washed with water and then dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was purified through a silica gel column chromatograph (chloroform/methanol=100/1 to 30/1 in volume ratio), thereby obtaining 0.5 g of oily 1,3-dimethyl-6-[4-(3-hydroxy-2-phenylpropyl)piperazin-1-yl]-2,4(1H,3H)-pyrimidinedione.

Workup

  1. additionadded
  2. additionwas added
  3. waitto stand overnight
  4. customAfterward, insolubles were removed from the solution by filtration
  5. concentrationthe filtrate was concentrated
  6. dissolutionthe resulting residue was then dissolved in ethyl acetate
  7. washThe obtained solution was washed with water
  8. dry with materialdried over anhydrous sodium sulfate
  9. distillationthe solvent was distilled off under reduced pressure
  10. customThe resulting residue was purified through a silica gel column chromatograph (chloroform/methanol=100/1 to 30/1 in volume ratio)

Sources & evidence

ORD record
ord-fa66836712b443b1b8690decd23d586f
Source dataset
uspto-grants-1994_05
Patent number
US05308848

Reaction notes

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