Cesium carbonate → 5-chloro-4-(1-(5-propylpyrimidin-2-yl)piperidin-4-yloxy)pyridin-2(1H)-one

HRID 1676210Notes

Reaction equation

HRID 1676210 reaction equation
CS([O:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[N:17]=[CH:16][C:15]([CH2:18][CH2:19][CH3:20])=[CH:14][N:13]=2)[CH2:8][CH2:7]1)(=O)=O.[Cl:21][C:22]1[C:23](O)=[CH:24][C:25](=[O:28])[NH:26][CH:27]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.CCOC(C)=O>[Cl:21][C:22]1[C:23]([O:5][CH:6]2[CH2:11][CH2:10][N:9]([C:12]3[N:17]=[CH:16][C:15]([CH2:18][CH2:19][CH3:20])=[CH:14][N:13]=3)[CH2:8][CH2:7]2)=[CH:24][C:25](=[O:28])[NH:26][CH:27]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 54679224GimeracilHCID 866262675-Propylpyrimidin-2-ylpiperidin-4-yl methanesulfonate

Product 1

HCID 673676265-chloro-4-(1-(5-propylpyrimidin-2-yl)piperidin-4-yloxy)pyridin-2(1H)-one

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 1-(5-propylpyrimidin-2-yl)piperidin-4-yl methanesulfonate (800 mg, 2.67 mmol), 5-chloro-4-hydroxypyridin-2(1H)-one (389 mg, 2.67 mmol, AK Scientific) and cesium carbonate (2612 mg, 8.02 mmol) in DMF (20 mL) was heated at 120° C. for 6 h. The reaction was cooled to rt, diluted with EtOAc (30 mL), and washed with H2O (3×). The organic layer was dried over Na2SO4 and concentrated under reduced pressure to give a yellow solid. The residue was purified by flash chromatography (SiO2, 0-10% MeOH/CH2Cl2) to give the desired product as a yellow solid. MS (ESI) 379 (M+H).

Workup

  1. temperatureThe reaction was cooled to rt
  2. washwashed with H2O (3×)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customto give a yellow solid
  6. customThe residue was purified by flash chromatography (SiO2, 0-10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-4e6f1f277b11487fa93aa23229b1a2c7
Source dataset
uspto-grants-2011_08
Patent number
US08003796B2

Reaction notes

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