Potassium Carbonate → HCID 57678383, compound

HRID 491473Notes

Reaction equation

HRID 491473 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.[C:19]([O:23][C:24]([N:26]1[CH2:37][CH2:36][C:29]2([C:33](=[O:34])[NH:32][C:31](=[O:35])[CH2:30]2)[CH2:28][CH2:27]1)=[O:25])([CH3:22])([CH3:21])[CH3:20].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:19]([O:23][C:24]([N:26]1[CH2:27][CH2:28][C:29]2([C:33](=[O:34])[N:32]([CH2:2][C:3]3[N:13]([CH2:14][C:15]([CH3:18])([CH3:17])[CH3:16])[C:6]4[N:7]=[C:8]([C:11]#[N:12])[N:9]=[CH:10][C:5]=4[CH:4]=3)[C:31](=[O:35])[CH2:30]2)[CH2:36][CH2:37]1)=[O:25])([CH3:22])([CH3:20])[CH3:21]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 113128256-Bromomethyl-7-(2,2-dimethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrileHCID 53234195tert-Butyl 1,3-dioxo-2,8-diazaspiro[4.5]decane-8-carboxylate

Product 1

HCID 57678383HCID 57678383, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-Bromomethyl-7-(2,2-dimethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile (1.0 g, 3.25 mmol) and 1,3-dioxo-2,8-diaza-spiro[4.5]decane-8-carboxylic acid tert-butyl ester (0.82 g, 3.42 mmol) are dissolved in DMF (15 ml) and potassium carbonate (0.58 g, 4.23 mmol) is added to the solution. The reaction mixture is stirred at room temperature for 15 h and quenched with saturated ammonium chloride and extracted with ethyl acetate. The combined extracts are washed with H2O, brine and dried over magnesium sulfate. Chromatography on silica gel (eluent; n-hexane:ethyl acetate=2:1) gives 1.56 g of desired 2-[2-cyano-7-(2,2-dimethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidin-6-ylmethyl]-1,3-dioxo-2,8-diaza-spiro[4.5]decane-8-carboxylic acid tert-butyl ester in 97% yield.

Workup

  1. customquenched with saturated ammonium chloride
  2. extractionextracted with ethyl acetate
  3. washThe combined extracts are washed with H2O, brine
  4. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-eb0a73e5004b486b8e9c0399afc9e730
Source dataset
uspto-grants-2009_05
Patent number
US07531546B2

Reaction notes

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