3-Bromopentane → 2-[(1-Ethylpropyl)amino]-5-mesityl-3,7-dimethyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one

HRID 598128Notes

Reaction equation

HRID 598128 reaction equation
[NH2:1][C:2]1[N:3]([CH3:22])[C:4](=[O:21])[C:5]2[C:10]([C:11]3[C:16]([CH3:17])=[CH:15][C:14]([CH3:18])=[CH:13][C:12]=3[CH3:19])=[CH:9][N:8]([CH3:20])[C:6]=2[N:7]=1.[H-].[Na+].Br[CH:26]([CH2:29][CH3:30])[CH2:27][CH3:28]>CN(C)C=O>[CH2:27]([CH:26]([NH:1][C:2]1[N:3]([CH3:22])[C:4](=[O:21])[C:5]2[C:10]([C:11]3[C:16]([CH3:17])=[CH:15][C:14]([CH3:18])=[CH:13][C:12]=3[CH3:19])=[CH:9][N:8]([CH3:20])[C:6]=2[N:7]=1)[CH2:29][CH3:30])[CH3:28]

Participants

5

Reactant 3

HCID 157383-BromopentaneHCID 24758Sodium hydride2×HCID 672673282-Amino-5-mesityl-3,7-dimethyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one

Product 1

HCID 589386242-[(1-Ethylpropyl)amino]-5-mesityl-3,7-dimethyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-oneYield 25%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-amino-5-mesityl-3,7-dimethyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one (0.062 g, 0.209 mmol) in N,N-dimethylformamide (0.5 mL) was added sodium hydride (66% in oil, 0.016 g, 0.439 mmol), and the mixture was allowed to stir at room temperature for 25 minutes. 3-Bromopentane (0.055 mL, 0.439 mmol) twice at room temperature and sodium hydride (66% in oil, 0.016 g, 0.439 mmol) at 0° C. was added during the reaction, stirring at room temperature for 15 hours and at 60° C. for 52 hours. After cooling, the reaction mixture was diluted with ice-cold water and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with hexane/ethyl acetate (4:1-2:1). The desired fractions were concentrated in vacuo. The residual crystals were washed with diisopropyl ether-hexane to give 0.019 g (25%) of the title compound.

Workup

  1. stirringstirring at room temperature for 15 hours and at 60° C. for 52 hours
  2. temperatureAfter cooling
  3. additionthe reaction mixture was diluted with ice-cold water
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water and brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel column chromatography
  9. washeluting with hexane/ethyl acetate (4:1-2:1)
  10. concentrationThe desired fractions were concentrated in vacuo
  11. washThe residual crystals were washed with diisopropyl ether-hexane

Sources & evidence

ORD record
ord-e6f0cbaf6e3747059784a26e73372940
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Reaction notes

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