Potassium Carbonate → 1-(5-Propylpyrimidin-2-yl)piperidin-4-ol

HRID 386540Notes

Reaction equation

HRID 386540 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([OH:7])[CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].Cl[C:15]1[N:20]=[CH:19][C:18]([CH2:21][CH2:22][CH3:23])=[CH:17][N:16]=1>CN(C=O)C.O>[CH2:21]([C:18]1[CH:17]=[N:16][C:15]([N:1]2[CH2:6][CH2:5][CH:4]([OH:7])[CH2:3][CH2:2]2)=[N:20][CH:19]=1)[CH2:22][CH3:23]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 79341Piperidin-4-olHCID 27357842-Chloro-5-propylpyrimidine

Product 1

HCID 670724781-(5-Propylpyrimidin-2-yl)piperidin-4-olYield 98.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a stirring solution of piperidin-4-ol (2.33 g, 23.0 mmol, Aldrich) and potassium carbonate (6.36 g, 46.0 mmol, EMD) in DMF (15 mL) at room temperature was added 2-chloro-5-propylpyrimidine (4.33 g, 27.6 mmol, Wako). The reaction mixture was heated at 100° C. for 3 h then diluted with H2O. The resulting mixture was extracted with EtOAc (2×). The organic layers were combined, dried over Na2SO4 and concentrated in vacuo to a brown oil. The oil was purified by flash chromatography (SiO2, 0 to 100% EtOAc in CH2Cl2) to yield 5.01 g of desired product as a white solid. MS (ESI) 222 (M+H).

Workup

  1. extractionThe resulting mixture was extracted with EtOAc (2×)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo to a brown oil
  4. customThe oil was purified by flash chromatography (SiO2, 0 to 100% EtOAc in CH2Cl2)

Sources & evidence

ORD record
ord-715907bd2b44474092b672cd654aa65a
Source dataset
uspto-grants-2013_02
Patent number
US08372837B2

Reaction notes

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