Hydrochloric Acid → HCID 17854684, compound

HRID 1727883Notes

Reaction equation

HRID 1727883 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[C:14]([C:15]([NH:17][CH2:18][CH2:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:16])=[C:13]([CH3:27])[N:12]=[C:11](SC)[N:10]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].ClC1C=CC=C(C(OO)=O)C=1.S([O-])([O-])=O.[Na+].[Na+].[BH4-].[Na+].Cl>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[C:14]([C:15]([NH:17][CH2:18][CH2:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:16])=[C:13]([CH3:27])[N:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acid3×HCID 4311764Sodium borohydrideHCID 10297376HCID 10297376, compound

Product 1

HCID 17854684HCID 17854684, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

100 mg (0.224 mmol) of 4-(3,4-dichlorophenyl)-6-methyl-2-(methylthio)-N-(3-phenylpropyl)-5-pyrimidinecarboxamide was dissolved in 5 ml of dichloromethane. 77.3 mg (0.448 mmol) of mCPBA (m-chloroperbenzoic acid; hereinafter abbreviated as mCPBA) was added thereto at 0° C. and stirred at the same temperature for 6 hours. 1 ml of saturated aqueous sodium sulfite solution was added thereto at the same temperature and stirred for 30 minutes heating to room temperature. After the reaction mixture was diluted with dichloromethane, the organic layer was washed with saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The obtained residue was dissolved in 5 ml of ethanol and 16.9 mg (0.448 mmol) of sodium borohydride was added at room temperature and stirred for 1 hour. 5 ml of 1N hydrochloric acid was added at the same temperature, stirred at room temperature for 30 minutes and then concentrated under reduced pressure. After the obtained residue was diluted with dichloromethane, the organic layer was washed with saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by the silica gel chromatography (hexane/ethyl acetate=3/1) to obtain the title compound.

Workup

  1. stirringat the same temperature and stirred for 30 minutes
  2. temperatureheating to room temperature
  3. washthe organic layer was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe obtained residue was dissolved in 5 ml of ethanol
  7. stirringstirred for 1 hour
  8. stirringstirred at room temperature for 30 minutes
  9. concentrationconcentrated under reduced pressure
  10. additionAfter the obtained residue was diluted with dichloromethane
  11. washthe organic layer was washed with saturated aqueous sodium chloride solution
  12. dry with materialdried over anhydrous magnesium sulfate
  13. concentrationconcentrated under reduced pressure
  14. customThe residue was purified by the silica gel chromatography (hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-e0c3043de7b34f61933763e8cbf2f396
Source dataset
uspto-grants-2009_02
Patent number
US07494989B2

Reaction notes

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