HCID 19012102, compound → HCID 21688812, compound

HRID 1729315Notes

Reaction equation

HRID 1729315 reaction equation
[CH3:1][N:2]1[C:7]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][O:17][C:18]3[CH:23]=[CH:22][C:21]([S:24][CH3:25])=[CH:20][C:19]=3[N+:26]([O-])=O)[CH2:10][CH2:9]2)=[CH:6][C:5](=[O:29])[N:4]([CH3:30])[C:3]1=[O:31]>C(O)C>[CH3:1][N:2]1[C:7]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][O:17][C:18]3[CH:23]=[CH:22][C:21]([S:24][CH3:25])=[CH:20][C:19]=3[NH2:26])[CH2:10][CH2:9]2)=[CH:6][C:5](=[O:29])[N:4]([CH3:30])[C:3]1=[O:31]

Participants

3

Reactant 1

HCID 19012102HCID 19012102, compound

Product 1

HCID 21688812HCID 21688812, compoundYield 33.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

2.0 g of the Compound v obtained in Reference Example 17 was dissolved in 20 ml of ethanol, and 4.5 g of stannic chloride (II) was added dropwise. The solution was heated up to 70° C. and then stirred for 30 minutes. The precipitated insolubles were removed by filtration, and the filtrate was then diluted with 100 ml of chloroform. Next, 20 ml of a 1N aqueous sodium hydroxide solution was added to the solution, followed by stirring vigorously. The formed insolubles were removed by filtration, and the resultant chloroform layer was separated, washed with water, dried over anhydrous sodium sulfate and then concentrated. The thus obtained oily product was purified through a silica gel column chromatograph (chloroform/methanol=100/1 in volume ratio), thereby obtaining 0.62 g of 1,3-dimethyl-6-[4-(3-[2-amino-4-methylmercaptophenoxy]propyl)piperazin-1-yl]-2,4(1H,3H)-pyrimidinedione (Compound 114).

Workup

  1. customThe precipitated insolubles were removed by filtration
  2. additionthe filtrate was then diluted with 100 ml of chloroform
  3. additionNext, 20 ml of a 1N aqueous sodium hydroxide solution was added to the solution
  4. stirringby stirring vigorously
  5. customThe formed insolubles were removed by filtration
  6. customthe resultant chloroform layer was separated
  7. washwashed with water
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated
  10. customThe thus obtained oily product was purified through a silica gel column chromatograph (chloroform/methanol=100/1 in volume ratio)

Sources & evidence

ORD record
ord-e1fd41f564104f3d9522d4ab01e8de6d
Source dataset
uspto-grants-1994_07
Patent number
US05332739

Reaction notes

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