Dichloromethane methanol → 4-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]tetrahydro-2H-thiopyran-4-ol 1,1-dioxide

HRID 410675Notes

Reaction equation

HRID 410675 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:19]2[S:23][C:22]([C:24]3([OH:30])[CH2:29][CH2:28][S:27][CH2:26][CH2:25]3)=[N:21][CH:20]=2)[CH:5]=[C:6]([NH:8][C:9]2[N:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[CH:11][N:10]=2)[CH:7]=1.C(Cl)Cl.CO.[OH2:36].[OH2:37].O.O.O.O.C(O[O-])(=O)C1C(=CC=CC=1)C([O-])=O.[Mg+2]>[O-]S([O-])(=S)=O.[Na+].[Na+].O>[CH3:1][C:2]1[CH:3]=[C:4]([C:19]2[S:23][C:22]([C:24]3([OH:30])[CH2:25][CH2:26][S:27](=[O:37])(=[O:36])[CH2:28][CH2:29]3)=[N:21][CH:20]=2)[CH:5]=[C:6]([NH:8][C:9]2[N:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[CH:11][N:10]=2)[CH:7]=1

Participants

6

Reactant 3

HCID 21226129Dichloromethane methanolHCID 21894687Magnesium 2-(dioxidan-2-ide-1-carbonyl)benzoate--water (1/1/6)HCID 672569944-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}-phenyl)-1,3-thiazol-2-yl]tetrahydro-2H-thiopyran-4-ol

Product 1

HCID 672587064-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]tetrahydro-2H-thiopyran-4-ol 1,1-dioxideYield 67.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 24477Sodium ThiosulfateSolvent

Procedure

4-[5-(3-Methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]tetrahydro-2H-thiopyran-4-ol (Step 1, Example 132, 300 mg, 0.663 mmol) was taken up in a 2:1 v/v CH2Cl2/MeOH mixture (6 mL) and magnesium monoperoxyphthalate hexahydrate (615 mg, 0.994 mmol) was added. The reaction was stirred at room temperature for 2 h, diluted with aqueous 10% Na2S2O3 and water and extracted with CH2Cl2 (2×). The combined organic layers were washed with brine, dried (MgSO4), filtered and evaporated. Column chromatography on silica (gradient elution, 0 to 75% EtOAc in hexanes) afforded 4-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]tetrahydro-2H-thiopyran-4-ol 1,1-dioxide (0.216 g, 0.446 mmol, 67% yield) as a yellow solid. MS ESI: [M+H]+ m/z 485.0.

Workup

  1. additionwas added
  2. extractionextracted with CH2Cl2 (2×)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-6011e57d439e40f18699a29af6335a4e
Source dataset
uspto-grants-2014_06
Patent number
US08759366B2

Reaction notes

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