Potassium Carbonate → HCID 68781024, compound

HRID 2264439Notes

Reaction equation

HRID 2264439 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5](Cl)=[N:6][CH:7]=1.[C:9]([O:13][C:14]([N:16]1[CH2:21][CH2:20][CH:19]([NH2:22])[CH2:18][CH2:17]1)=[O:15])([CH3:12])([CH3:11])[CH3:10].C([O-])([O-])=O.[K+].[K+]>CC(N(C)C)=O>[C:9]([O:13][C:14]([N:16]1[CH2:21][CH2:20][CH:19]([NH:22][C:5]2[N:4]=[CH:3][C:2]([Br:1])=[CH:7][N:6]=2)[CH2:18][CH2:17]1)=[O:15])([CH3:12])([CH3:10])[CH3:11]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 6066655-Bromo-2-chloropyrimidineHCID 12682914-Amino-1-Boc-piperidine

Product 1

HCID 68781024HCID 68781024, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of 5-bromo-2-chloro-pyrimidine (3.0 g, 15.51 mmol, 1.0 equiv; commercially available) and 4-amino-piperidine-1-carboxylic acid tert-butyl ester (3.42 g, 17.06 mmol, 1.1 equiv; commercially available) in DMAc (50 mL) was added anhydrous K2CO3 (5.36 g, 38.78 mmol, 2.5 equiv) and the reaction mixture stirred at rt for 18 h. The reaction mixture was heated for an additional time period of 2 h to 60° C. and then extracted with ethyl acetate (3×100 mL) and the combined organic phases washed with a sat. solution of sodium chloride (2×50 mL). The organic phase was dried over MgSO4, concentrated by evaporation under reduced pressure and the residue purified by silica column chromatography using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of heptane/ethyl acetate providing 2.22 g (40%) of the title compound. MS (ISP): 357.0 [M+H]+.

Workup

  1. temperatureThe reaction mixture was heated for an additional time period of 2 h to 60° C.
  2. extractionextracted with ethyl acetate (3×100 mL)
  3. washthe combined organic phases washed with a sat. solution of sodium chloride (2×50 mL)
  4. dry with materialThe organic phase was dried over MgSO4
  5. concentrationconcentrated by evaporation under reduced pressure
  6. customthe residue purified by silica column chromatography
  7. washeluting with a gradient of heptane/ethyl acetate providing 2.22 g (40%) of the title compound

Sources & evidence

ORD record
ord-d812b85e5aa04b029c4f80a615ce5a9d
Source dataset
uspto-grants-2010_12
Patent number
US07855194B2

Reaction notes

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