1,5-Dibromopentane → 5-mesityl-3,7-dimethyl-2-(piperidin-1-yl)-3H-pyrrolo[2,3-d]pyrimidin-4(7H)-one

HRID 598127Notes

Reaction equation

HRID 598127 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.Br[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]Br.[H-].[Na+]>CN(C)C=O>[C:12]1([CH3:19])[CH:13]=[C:14]([CH3:18])[CH:15]=[C:16]([CH3:17])[C:11]=1[C:10]1[C:5]2[C:4](=[O:21])[N:3]([CH3:22])[C:2]([N:1]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)=[N:7][C:6]=2[N:8]([CH3:20])[CH:9]=1

Participants

5

Reactant 3

HCID 81001,5-DibromopentaneHCID 24758Sodium hydrideHCID 672673282-Amino-5-mesityl-3,7-dimethyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one

Product 1

HCID 545829625-mesityl-3,7-dimethyl-2-(piperidin-1-yl)-3H-pyrrolo[2,3-d]pyrimidin-4(7H)-oneYield 67.3%

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 (0.063 g, 0.212 mmol) in N,N-dimethylformamide (1 mL) was added 1,5-dibromopentane (0.029 mL, 0.212 mmol) and sodium hydride (66% in oil, 0.015 g, 0.426 mmol) at 0° C., and the mixture was allowed to stir at room temperature for 1 hour. 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 (10:1-3:1). The oil obtained was crystallized from diisopropyl ether-hexane to give 0.052 g (67%) of the title compound.

Workup

  1. additionThe reaction mixture was diluted with ice-cold water
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography
  7. washeluting with hexane/ethyl acetate (10:1-3:1)
  8. customThe oil obtained
  9. customwas crystallized from diisopropyl ether-hexane

Sources & evidence

ORD record
ord-52f95f159ddd4592b6026ca191602611
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Reaction notes

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