Cesium carbonate → 4-(4-(2,2-Dimethyl-1,3-dioxan-5-yl)phenoxy)-5-methyl-6-(1-(pyrimidin-2-yl)piperidin-4-yloxy)pyrimidine

HRID 1619444Notes

Reaction equation

HRID 1619444 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].Cl[C:8]1[C:13]([CH3:14])=[C:12]([O:15][CH:16]2[CH2:21][CH2:20][N:19]([C:22]3[N:27]=[CH:26][CH:25]=[CH:24][N:23]=3)[CH2:18][CH2:17]2)[N:11]=[CH:10][N:9]=1.[CH3:28][C:29]1([CH3:42])[O:34][CH2:33][CH:32]([C:35]2[CH:40]=[CH:39][C:38]([OH:41])=[CH:37][CH:36]=2)[CH2:31][O:30]1>CN(C=O)C>[CH3:28][C:29]1([CH3:42])[O:30][CH2:31][CH:32]([C:35]2[CH:40]=[CH:39][C:38]([O:41][C:8]3[C:13]([CH3:14])=[C:12]([O:15][CH:16]4[CH2:21][CH2:20][N:19]([C:22]5[N:27]=[CH:26][CH:25]=[CH:24][N:23]=5)[CH2:18][CH2:17]4)[N:11]=[CH:10][N:9]=3)=[CH:37][CH:36]=2)[CH2:33][O:34]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 675102564-(2,2-Dimethyl-1,3-dioxan-5-yl)phenolHCID 866651634-Chloro-5-methyl-6-(1-(pyrimidin-2-yl)piperidin-4-yloxy)pyrimidine

Product 1

HCID 675115354-(4-(2,2-Dimethyl-1,3-dioxan-5-yl)phenoxy)-5-methyl-6-(1-(pyrimidin-2-yl)piperidin-4-yloxy)pyrimidineYield 68.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Cesium carbonate (2.97 mg, 0.00914 moles) was added to a solution 4-chloro-5-methyl-6-(1-(pyrimidin-2-yl)piperidin-4-yloxy)pyrimidine (1.39 gm, 0.00457 moles) and 4-(2,2-dimethyl-1,3-dioxan-5-yl)phenol (950 mg, 0.00457 moles) in dry DMF (10 ml) and the reaction mixture was stirred at 60° C. for 12 hours. Then reaction mixture was 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 1.5 gm product as white solid.

Workup

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

Sources & evidence

ORD record
ord-8a17741720f0431eb858ecd613c322b0
Source dataset
uspto-grants-2014_07
Patent number
US08772302B2

Reaction notes

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