Dimethylformamide → 2-amino-3-isopropyl-5-mesityl-7-methyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one

HRID 598125Notes

Reaction equation

HRID 598125 reaction equation
[NH2:1][C:2]1[NH:3][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.CN(C)C=O.[H-].[Na+].I[CH:30]([CH3:32])[CH3:31]>O>[NH2:1][C:2]1[N:3]([CH:30]([CH3:32])[CH3:31])[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

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 6362Isopropyl iodideHCID 24758Sodium hydrideHCID 1364007122-Amino-5-mesityl-7-methyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one

Product 1

HCID 672672412-amino-3-isopropyl-5-mesityl-7-methyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-oneYield 49.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 2-amino-5-mesityl-7-methyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one (156 mg, 0.55 mmol) and N,N-dimethylformamide (5 ml) was added sodium hydride (60% in oil, 24 mg, 0.60 mmol) at 0° C. and stirred for 0.5 hour. After stirring at room temperature for 0.5 hour, to the mixture was added a solution of 2-iodopropane (102 mg, 0.60 mmol) and N,N-dimethylformamide (2 ml) at 0° C. and stirred for 0.5 hour. After stirring at room temperature for 3 hours, the mixture was diluted with water (20 ml) and extracted with ethyl acetate (50 ml×2). The extracts were combined, washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel chromatography eluting with hexane/ethyl acetate (3:1) to give 88 mg (49%) of the title compound.

Workup

  1. stirringAfter stirring at room temperature for 0.5 hour, to the mixture
  2. stirringstirred for 0.5 hour
  3. stirringAfter stirring at room temperature for 3 hours
  4. extractionextracted with ethyl acetate (50 ml×2)
  5. washwashed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel chromatography
  9. washeluting with hexane/ethyl acetate (3:1)

Sources & evidence

ORD record
ord-fe8fabb6da4642578a711ab150ef7ce0
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Reaction notes

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