Potassium Carbonate → HCID 59834631, compound

HRID 271620Notes

Reaction equation

HRID 271620 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[N:7]1[CH2:18][CH2:17][C:10]2([NH:14][C:13](=[O:15])[NH:12][C:11]2=[O:16])[CH2:9][CH2:8]1.C([O-])([O-])=O.[K+].[K+].Br[CH2:26][C:27]1[N:37]([CH2:38][C:39]([CH3:42])([CH3:41])[CH3:40])[C:30]2[N:31]=[C:32]([C:35]#[N:36])[N:33]=[CH:34][C:29]=2[CH:28]=1>CN(C=O)C>[CH3:40][C:39]([CH3:42])([CH3:41])[CH2:38][N:37]1[C:30]2[N:31]=[C:32]([C:35]#[N:36])[N:33]=[CH:34][C:29]=2[CH:28]=[C:27]1[CH2:26][N:12]1[C:11](=[O:16])[C:10]2([CH2:9][CH2:8][N:7]([C:2]3[N:3]=[CH:4][CH:5]=[CH:6][N:1]=3)[CH2:18][CH2:17]2)[NH:14][C:13]1=[O:15]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 113128256-Bromomethyl-7-(2,2-dimethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrileHCID 17968186HCID 17968186, compound

Product 1

HCID 59834631HCID 59834631, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 180.0 mg (0.728 mmoles) of 8-pyrimidin-2-yl-1,3,8-triaza-spiro[4.5]decane-2,4-dione in 2.0 ml of DMF, 99.4 mg (0.719 mmoles) of K2CO3 and 170.0 mg (0.553 mmoles) of 6-bromomethyl-7-(2,2-dimethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile are added at ambient temperature. The mixture is stirred for 5 hours at ambient temperature and filtered. The mixture is diluted with AcOEt and H2O, and then extracted with AcOEt. The combined extracts are washed with water and brine, dried over MgSO4 and concentrated under reduced pressure. The residue is purified by silica gel column chromatography to give 151.5 mg of desired 7-(2,2-dimethyl-propyl)-6-(2,4-dioxo-8-pyrimidin-2-yl-1,3,8-triaza-spiro[4.5]dec-3-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile in 58% yield.

Workup

  1. filtrationfiltered
  2. additionThe mixture is diluted with AcOEt and H2O
  3. extractionextracted with AcOEt
  4. washThe combined extracts are washed with water and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-962b81d6ed1841f5aad7b49e139e779e
Source dataset
uspto-grants-2008_11
Patent number
US07452886B2

Reaction notes

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