Hydrochloric Acid → 2-Methanesulfonyl-4-(2-piperidin-1-yl-ethoxy)-6-(3-trifluoromethyl phenyl)-pyrimidine

HRID 2053102Notes

Reaction equation

HRID 2053102 reaction equation
Cl.CS[C:4]1[N:9]=[C:8]([O:10][CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[CH:7]=[C:6]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=2)[N:5]=1.O[O:30][S:31]([O-:33])=O.[K+].[C:35]([O-])([O-])=O.[Na+].[Na+]>CCOCC.CCOC(C)=O>[CH3:35][S:31]([C:4]1[N:9]=[C:8]([O:10][CH2:11][CH2:12][N:13]2[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]2)[CH:7]=[C:6]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:26])[F:27])[CH:20]=2)[N:5]=1)(=[O:33])=[O:30]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 23707502Potassium hydroxy sulfiteHCID 688256192-Methylthio-4-(2-piperidin-1-yl-ethoxy)-6-(3-trifluoromethyl-phenyl)-pyrimidine

Product 1

HCID 688229302-Methanesulfonyl-4-(2-piperidin-1-yl-ethoxy)-6-(3-trifluoromethyl phenyl)-pyrimidineYield 90%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of HCl (720 μl, 2N in Et2O, 1.43 mmol) was added to a solution of 2-methylthio-4-(2-piperidin-1-yl-ethoxy)-6-(3-trifluoromethyl-phenyl)-pyrimidine (190 mg, 0.48 mmol) in Et2O (1 ml). The solvent was evaporated and the precipitate was dissolved in a mixture of water (1 ml) and acetonitrile (6 ml). Oxone (586 mg, 0.96 mmol) was added and the reaction mixture was stirred at room temperature for 60 h. An aqueous Na2CO3 saturated solution (6 ml) was added (pH=9) followed by AcOEt. The organic layer was washed with Na2SO3, with brine, dried over MgSO4 and concentrated under reduced pressure to give the above titled compound: 184 mg (yield: 90%) which was used in the next step without any further purification.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe precipitate was dissolved in a mixture of water (1 ml) and acetonitrile (6 ml)
  3. washThe organic layer was washed with Na2SO3, with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4f327586a6944f1a9038b9ba9bebf964
Source dataset
uspto-grants-2008_02
Patent number
US07326715B2

Reaction notes

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