Piperidine → Methyl 2-(4-methyl-2-phenyl-6-(piperidin-1-yl)pyrimidin-5-yl)pentanoate

HRID 1399627Notes

Reaction equation

HRID 1399627 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[C:8]1[C:13]([CH:14]([CH2:19][CH2:20][CH3:21])[C:15]([O:17][CH3:18])=[O:16])=[C:12]([CH3:22])[N:11]=[C:10]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:9]=1>O1CCCC1.C(=O)([O-])O.[Na+]>[CH3:22][C:12]1[C:13]([CH:14]([CH2:19][CH2:20][CH3:21])[C:15]([O:17][CH3:18])=[O:16])=[C:8]([N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[N:9]=[C:10]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:11]=1

Participants

5

Reactant 2

HCID 8082PiperidineHCID 86665652Methyl 2-(4-chloro-6-methyl-2-phenylpyrimidin-5-yl)pentanoate

Product 1

HCID 66955957Methyl 2-(4-methyl-2-phenyl-6-(piperidin-1-yl)pyrimidin-5-yl)pentanoateYield 51.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Piperidine (0.198 mL; 2.00 mmol) was added to a solution of methyl 2-(4-chloro-6-methyl-2-phenylpyrimidin-5-yl)pentanoate (0.159 g; 0.5 mmol) in tetrahydrofuran (1.5 mL) and the reaction mixture was irradiated in a microwave oven at 100° C. for 30 min. The mixture was diluted with a saturated solution of sodium hydrogen carbonate and was extracted with ethyl acetate. The combined organics were washed with brine, dried over magnesium sulphate and concentrated under reduced pressure. Purification by flash-chromatography on silica gel using a gradient of ethyl acetate (2-40%) in heptane furnished 0.094 g (51%) of the title compound.

Workup

  1. customthe reaction mixture was irradiated in a microwave oven at 100° C. for 30 min
  2. extractionwas extracted with ethyl acetate
  3. washThe combined organics were washed with brine
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customPurification by flash-chromatography on silica gel using a gradient of ethyl acetate (2-40%) in heptane

Sources & evidence

ORD record
ord-393e3097ae1749f787eb0fb53e31fa31
Source dataset
uspto-grants-2014_12
Patent number
US08906906B2

Reaction notes

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