Hydrochloric Acid → HCID 17854567, compound

HRID 1727896Notes

Reaction equation

HRID 1727896 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](S(C)(=O)=O)[N:10]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[CH2:32]([Mg]Br)[CH3:33].Cl>C1COCC1.C(OCC)(=O)C>[CH2:32]([C:11]1[N:10]=[C:9]([C:4]2[CH:3]=[C:2]([Cl:1])[CH:7]=[C:6]([Cl:8])[CH:5]=2)[C:14]([C:15]([NH:17][CH2:18][CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:16])=[C:13]([CH3:27])[N:12]=1)[CH3:33]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 17854585HCID 17854585, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 17854567HCID 17854567, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

100 mg (0.209 mmol) of 4-(3,5-dichlorophenyl)-6-methyl-2-(methylsulfonyl)-N-(3-phenylpropyl)-5-pyrimidinecarboxamide was dissolved in 3 ml of THF. 0.314 ml (13% THF solution, 1 mol/l) of ethylmagnesium bromide was added at 0° C. and stirred at the same temperature for 1 hour. 10% hydrochloric acid was added at the same temperature and stirred for 10 minutes. After the reaction mixture was diluted with ethyl acetate, 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=10/1 to 1/1) to obtain the title compound.

Workup

  1. stirringstirred for 10 minutes
  2. washthe organic layer was washed with saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by the silica gel chromatography (hexane/ethyl acetate=10/1 to 1/1)

Sources & evidence

ORD record
ord-fcfa8fa262904839a5835cb1108c6f3d
Source dataset
uspto-grants-2009_02
Patent number
US07494989B2

Reaction notes

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