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

HRID 1676209Notes

Reaction equation

HRID 1676209 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([OH:7])[CH2:3][CH2:2]1.Cl[C:9]1[N:14]=[CH:13][C:12]([CH2:15][CH2:16][CH3:17])=[CH:11][N:10]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.CCOC(C)=O>[CH2:15]([C:12]1[CH:11]=[N:10][C:9]([N:1]2[CH2:6][CH2:5][CH:4]([OH:7])[CH2:3][CH2:2]2)=[N:14][CH:13]=1)[CH2:16][CH3:17]

Participants

6

Reactant 3

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

Product 1

HCID 670724781-(5-Propylpyrimidin-2-yl)piperidin-4-ol

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

A suspension of piperidin-4-ol (12 g, 119 mmol), 2-chloro-5-propylpyrimidine (20.44 g, 131 mmol) and potassium carbonate (49.2 g, 356 mmol) in DMF (100 mL) was heated at 110° C. for 12 h and cooled to rt. The mixture was diluted with EtOAc (250 ml) and washed with H2O (3×). After drying over Na2SO4, the organic layer was evaporated to give a yellow oil. The crude oil was purified on a flash chromatography (SiO2, 0 to 10% MeOH/CH2Cl2) to give a yellow solid. MS (ESI) 222 (M+H).

Workup

  1. temperaturecooled to rt
  2. washwashed with H2O (3×)
  3. dry with materialAfter drying over Na2SO4
  4. customthe organic layer was evaporated
  5. customto give a yellow oil
  6. customThe crude oil was purified on a flash chromatography (SiO2, 0 to 10% MeOH/CH2Cl2)
  7. customto give a yellow solid

Sources & evidence

ORD record
ord-1b6f10650041404687e51150486f5a58
Source dataset
uspto-grants-2011_08
Patent number
US08003796B2

Reaction notes

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