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

HRID 1895704Notes

Reaction equation

HRID 1895704 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+].CO.C(Cl)Cl>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

7

Reactant 4

HCID 11430Potassium CarbonateHCID 79341Piperidin-4-olHCID 27357842-Chloro-5-propylpyrimidineHCID 21226129Dichloromethane methanol

Product 1

HCID 670724781-(5-Propylpyrimidin-2-yl)piperidin-4-olYield 72.4%

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. The mixture was diluted with EtOAc (250 ml) and washed three times with water, dried over Na2SO4, and concentrated to give a yellow oil. The oil was purified by flash chromatography (SiO2, O-10% MeOH/CH2Cl2) to yield product (19 g, 86 mmol, 72.4% yield) as yellow solid. MS (ESI) 222.2 (M+1).

Workup

  1. washwashed three times with water
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customto give a yellow oil
  5. customThe oil was purified by flash chromatography (SiO2

Sources & evidence

ORD record
ord-1fb5adacf9614fa5827376b665b23dec
Source dataset
uspto-grants-2013_08
Patent number
US08513424B2

Reaction notes

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