Potassium Carbonate → (2R,3R)-2-(2,4-difluorophenyl)-3-((1-(pyrimidin-2-yl)piperidin-4-yl)oxy)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol

HRID 1430085Notes

Reaction equation

HRID 1430085 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[N:7]1[CH2:12][CH2:11][CH:10]([OH:13])[CH2:9][CH2:8]1.CC(C)([O-])C.[K+].[F:20][C:21]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:22]=1[C@@:28]1([CH2:32][N:33]2[CH:37]=[N:36][CH:35]=[N:34]2)[C@@H:30]([CH3:31])[O:29]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C>[F:20][C:21]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:22]=1[C@:28]([OH:29])([C@H:30]([O:13][CH:10]1[CH2:9][CH2:8][N:7]([C:2]2[N:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[CH2:12][CH2:11]1)[CH3:31])[CH2:32][N:33]1[CH:37]=[N:36][CH:35]=[N:34]1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 107058781-(((2R,3R)-2-(2,4-difluorophenyl)-3-methyloxiran-2-yl)methyl)-1H-1,2,4-triazoleHCID 202340981-(Pyrimidin-2-yl)piperidin-4-olHCID 23665647Potassium tert-butoxide

Product 1

HCID 67367867(2R,3R)-2-(2,4-difluorophenyl)-3-((1-(pyrimidin-2-yl)piperidin-4-yl)oxy)-1-(1H-1,2,4-triazol-1-yl)butan-2-olYield 21%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-(pyrimidin-2-yl)piperidin-4-ol (19.4 mg, 0.08 mmol) in N,N-dimethylformamide (0.5 mL) was added potassium tert-butoxide (10.7 mg, 0.01 mmol), followed by stirring at room temperature for 2 hrs. The resulting solution was mixed with 1-(((2R,3R)-2-(2,4-difluorophenyl)-3-methyloxiran-2-yl)methyl)-1H-1,2,4-triazole (20.0 mg, 0.08 mmol) and anhydrous potassium carbonate (13.2 mg, 0.01 mmol) and stirred at room temperature for one hr. The resulting reaction mixture was diluted with ethyl acetate, and washed with a saturated aqueous ammonium chloride solution and then with saline to separate an organic solvent layer. The organic solvent layer was dried over anhydrous magnesium sulfate and concentrated by evaporation at reduced pressure. The concentrate was purified using silica gel chromatography to afford the title compound (yield 21%).

Workup

  1. stirringstirred at room temperature for one hr
  2. customThe resulting reaction mixture
  3. washwashed with a saturated aqueous ammonium chloride solution
  4. customwith saline to separate an organic solvent layer
  5. dry with materialThe organic solvent layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated by evaporation at reduced pressure
  7. customThe concentrate was purified

Sources & evidence

ORD record
ord-709f1cc0cd4f4cf186592b32e877c7c6
Source dataset
uspto-grants-2015_01
Patent number
US08940768B2

Reaction notes

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