Potassium Carbonate → HCID 9880368, compound

HRID 271575Notes

Reaction equation

HRID 271575 reaction equation
Br[CH2:2][C:3]1[N:13]([CH2:14][C:15]([CH3:18])([CH3:17])[CH3:16])[C:6]2[N:7]=[C:8]([C:11]#[N:12])[N:9]=[CH:10][C:5]=2[CH:4]=1.[NH:19]1[CH2:24][CH2:23][C:22](=[O:25])[CH2:21][CH2:20]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:16][C:15]([CH3:18])([CH3:17])[CH2:14][N:13]1[C:6]2[N:7]=[C:8]([C:11]#[N:12])[N:9]=[CH:10][C:5]=2[CH:4]=[C:3]1[CH2:2][N:19]1[CH2:24][CH2:23][C:22](=[O:25])[CH2:21][CH2:20]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 337214-PiperidoneHCID 113128256-Bromomethyl-7-(2,2-dimethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile

Product 1

HCID 9880368HCID 9880368, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 100 mg (0.32 mmoles) of 6-bromomethyl-7-(2,2-dimethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile and 150 mg (0.96 mmoles) of piperidin-4-one in 5 ml of DMF, 88 mg (0.64 mmoles) of K2CO3 is added at ambient temperature. After being stirred for 18 hours, the reaction mixture is quenched with H2O and the mixture is extracted with AcOEt. The combined extracts are washed with brine, dried over MgSO4 and concentrated under reduced pressure. The residue is purified by silica gel column chromatography to give 96 mg of disired 7-(2,2-dimethyl-propyl)-6-(4-oxo-piperidin-1-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile in 92% yield.

Workup

  1. customthe reaction mixture is quenched with H2O
  2. extractionthe mixture is extracted with AcOEt
  3. washThe combined extracts are washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-4aa7aba789d548888c4aa47fc2d62c97
Source dataset
uspto-grants-2008_11
Patent number
US07452886B2

Reaction notes

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