Potassium Carbonate → 7-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1,7-diazaspiro[4.5]decane-1-carboxylic acid tert-butyl ester

HRID 1912444Notes

Reaction equation

HRID 1912444 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:12]2([CH2:17][CH2:16][CH2:15][NH:14][CH2:13]2)[CH2:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[C:19]1[C:20]2[CH:27]=[CH:26][NH:25][C:21]=2[N:22]=[CH:23][N:24]=1.C(=O)([O-])[O-].[K+].[K+]>O>[C:1]([O:5][C:6]([N:8]1[C:12]2([CH2:17][CH2:16][CH2:15][N:14]([C:19]3[C:20]4[CH:27]=[CH:26][NH:25][C:21]=4[N:22]=[CH:23][N:24]=3)[CH2:13]2)[CH2:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 53566827H-Pyrrolo(2,3-d)pyrimidine, 4-chloro-HCID 24741699tert-Butyl 1,7-diazaspiro[4.5]decane-1-carboxylate

Product 1

HCID 582933867-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1,7-diazaspiro[4.5]decane-1-carboxylic acid tert-butyl esterYield 79.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

1,7-Diazaspiro[4.5]decane-1-carboxylic acid tert-butyl ester (51 mg) was mixed with 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (36 mg), potassium carbonate (59 mg) and water (1 ml), and the mixture was stirred for 1.5 hours with refluxing. The mixture was cooled to room temperature, and thereto was added water. The mixture was extracted with chloroform. The organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=1/1, followed by chloroform/methanol=20/1) to give the titled compound (60 mg).

Workup

  1. temperaturewith refluxing
  2. extractionThe mixture was extracted with chloroform
  3. washThe organic layer was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=1/1, followed by chloroform/methanol=20/1)

Sources & evidence

ORD record
ord-8a3286d4084e4c518273d500b87dc0f0
Source dataset
uspto-grants-2013_12
Patent number
US08609647B2

Reaction notes

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