Chlorotrimethylsilane → HCID 10049493, compound

HRID 1729294Notes

Reaction equation

HRID 1729294 reaction equation
[NH2:1][C:2]1[CH:27]=[CH:26][C:5]([O:6][CH2:7][CH2:8][CH2:9][N:10]2[CH2:15][CH2:14][N:13]([C:16]3[N:21]([CH3:22])[C:20](=[O:23])[N:19]([CH3:24])[C:18](=[O:25])[CH:17]=3)[CH2:12][CH2:11]2)=[CH:4][CH:3]=1.C[Si](Cl)(C)C.[CH3:33][S:34](Cl)(=[O:36])=[O:35].[OH-].[Na+]>O.N1C=CC=CC=1.O1CCOCC1>[CH3:22][N:21]1[C:16]([N:13]2[CH2:12][CH2:11][N:10]([CH2:9][CH2:8][CH2:7][O:6][C:5]3[CH:26]=[CH:27][C:2]([NH:1][S:34]([CH3:33])(=[O:36])=[O:35])=[CH:3][CH:4]=3)[CH2:15][CH2:14]2)=[CH:17][C:18](=[O:25])[N:19]([CH3:24])[C:20]1=[O:23]

Participants

8

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 14798Sodium HydroxideHCID 31297Methanesulfonyl chlorideHCID 10090741HCID 10090741, compound

Product 1

HCID 10049493HCID 10049493, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1049PyridineSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

20 ml of a dioxane solution containing 1.1 g of 6-[4-(3-[4-aminophenoxy]propyl)piperazin-1-yl]-1,3-dimethyl-2,4(1H,3H)-pyrimidinedione obtained in Example 6 and 1.8 ml of pyridine was cooled to 0° C., and 0.95 ml of trimethylsilyl chloride was further added, followed by stirring at the same temperature for 5 minutes and then at room temperature for 30 minutes. The reaction solution was cooled to 0° C. again, and 0.6 ml of methanesulfonyl chloride was added dropwise thereto. The solution was stirred at the same temperature for 5 minutes and further at room temperature for 1 hour, and then cooled on an ice water bath. Afterward, 10 ml of ice water was added dropwise, and 50 ml of water and 70 ml of a 1N aqueous sodium hydroxide solution were further added. The resultant aqueous solution was washed with chloroform (500 ml×2), made weakly acidic with concentrated hydrochloric acid and then washed with chloroform (50 ml). In succession, potassium carbonate was added to this solution to adjust its pH to 7, and the solution was extracted with chloroform (50 ml×3), dried over sodium sulfate and then concentrated to obtain 0.9 g of crystalline 1,3-dimethyl-6-[4-(3-[4-methanesulfonylaminophenoxy]propyl)piperazin-1-yl]-2,4(1H,3H)-pyrimidinedione.

Workup

  1. waitat room temperature for 30 minutes
  2. temperatureThe reaction solution was cooled to 0° C. again
  3. stirringThe solution was stirred at the same temperature for 5 minutes and further at room temperature for 1 hour
  4. temperaturecooled on an ice water bath
  5. washThe resultant aqueous solution was washed with chloroform (500 ml×2)
  6. washwashed with chloroform (50 ml)
  7. additionIn succession, potassium carbonate was added to this solution
  8. extractionthe solution was extracted with chloroform (50 ml×3)
  9. dry with materialdried over sodium sulfate
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-b9f2805f8ef342588e150cbad0284151
Source dataset
uspto-grants-1994_07
Patent number
US05332739

Reaction notes

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