Potassium Carbonate → HCID 68779156, compound

HRID 2264510Notes

Reaction equation

HRID 2264510 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[N:20]=[CH:19][C:18]([OH:21])=[CH:17][N:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:29][C:30]#[N:31]>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([NH:14][C:15]2[N:20]=[CH:19][C:18]([O:21][CH2:29][C:30]#[N:31])=[CH:17][N:16]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 68779108HCID 68779108, compound

Product 1

HCID 68779156HCID 68779156, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 4-(5-hydroxy-pyrimidin-2-ylamino)-piperidine-1-carboxylic acid tert-butyl ester (0.74 g, 2.5 mmol, 1.0 equiv; intermediate C31/step 2) in DMF (10 mL) was added potassium carbonate (1.05 g, 7.5 mmol, 3.0 equiv), followed by bromoacetonitrile (0.21 mL, 0.37 g, 3.0 mmol, 1.2 equiv). After 90 min, the reaction mixture was poured into ice water and extracted twice with diethylether. The combined organic layers were washed with water, dried over MgSO4, filtered and concentrated by evaporation under reduced pressure. The crude product was purified by column chromatography on silica eluting with a gradient of dichloromethane/methanol to give 0.70 g (84%) of the title compound as a light yellow solid. MS (ISP): 334.3 [M+H]+.

Workup

  1. extractionextracted twice with diethylether
  2. washThe combined organic layers were washed with water
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated by evaporation under reduced pressure
  6. customThe crude product was purified by column chromatography on silica eluting with a gradient of dichloromethane/methanol

Sources & evidence

ORD record
ord-9ee336451b59439f984d3dc384ef4eae
Source dataset
uspto-grants-2010_12
Patent number
US07855194B2

Reaction notes

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