Cesium carbonate → 4-((4-(2,2-Dimethyl-1,3-dioxan-5-yl)phenoxy)methyl)-2-(1-(pyrimidin-2-yl)piperidin-4-yl)thiazole

HRID 1619446Notes

Reaction equation

HRID 1619446 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].CS([O:11][CH2:12][C:13]1[N:14]=[C:15]([CH:18]2[CH2:23][CH2:22][N:21]([C:24]3[N:29]=[CH:28][CH:27]=[CH:26][N:25]=3)[CH2:20][CH2:19]2)[S:16][CH:17]=1)(=O)=O.[CH3:30][C:31]1([CH3:44])[O:36][CH2:35][CH:34]([C:37]2[CH:42]=[CH:41][C:40](O)=[CH:39][CH:38]=2)[CH2:33][O:32]1>CN(C=O)C>[CH3:30][C:31]1([CH3:44])[O:32][CH2:33][CH:34]([C:37]2[CH:42]=[CH:41][C:40]([O:11][CH2:12][C:13]3[N:14]=[C:15]([CH:18]4[CH2:23][CH2:22][N:21]([C:24]5[N:29]=[CH:28][CH:27]=[CH:26][N:25]=5)[CH2:20][CH2:19]4)[S:16][CH:17]=3)=[CH:39][CH:38]=2)[CH2:35][O:36]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 675102564-(2,2-Dimethyl-1,3-dioxan-5-yl)phenolHCID 86665164(2-(1-(Pyrimidin-2-yl)piperidin-4-yl)thiazol-4-yl)methyl methanesulfonate

Product 1

HCID 675101514-((4-(2,2-Dimethyl-1,3-dioxan-5-yl)phenoxy)methyl)-2-(1-(pyrimidin-2-yl)piperidin-4-yl)thiazoleYield 114.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Cesium carbonate (735 mg, 0.0022 moles) was added to a solution of (2-(1-(pyrimidin-2-yl)piperidin-4-yl)thiazol-4-yl)methyl methanesulfonate (490 gm, 0.00112 moles) and 4-(2,2-dimethyl-1,3-dioxan-5-yl)phenol (281 mg, 0.001384 moles) in DMF (10 ml) and the reaction mixture was stirred at 60° C. for 2 hours. Then the reaction mixture was then poured into ice cold water and extracted with ethyl acetate. The organic extract was successively washed with water & brine, dried over sodium sulfate and concentrated under reduced pressure. The crude product so obtained was purified by column chromatography (silica gel) using 22% ethyl acetate in hexane as eluent to obtain 600 mg product as white solid.

Workup

  1. additionThen the reaction mixture was then poured into ice cold water
  2. extractionextracted with ethyl acetate
  3. extractionThe organic extract
  4. washwas successively washed with water & brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product so obtained
  8. customwas purified by column chromatography (silica gel)

Sources & evidence

ORD record
ord-d22b4ba1dc814256b05d29b7481e2133
Source dataset
uspto-grants-2014_07
Patent number
US08772302B2

Reaction notes

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