Dimethylformamide → 2-(dibutylamino)-5-mesityl-3,7-dimethyl-3H-pyrrolo[2,3-d]pyrimidin-4(7H)-one

HRID 598121Notes

Reaction equation

HRID 598121 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.CN(C)C=O.[H-].[Na+].[CH2:30](I)[CH2:31][CH2:32][CH3:33]>O>[CH2:30]([N:1]([CH2:4][CH2:5][CH2:10][CH3:9])[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)[CH2:31][CH2:32][CH3:33]

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 10962Butyl iodideHCID 24758Sodium hydrideHCID 672673282-Amino-5-mesityl-3,7-dimethyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one

Product 1

HCID 545809612-(dibutylamino)-5-mesityl-3,7-dimethyl-3H-pyrrolo[2,3-d]pyrimidin-4(7H)-oneYield 122.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 2-amino-5-mesityl-3,7-dimethyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one (100 mg, 0.34 mmol) and N,N-dimethylformamide (2 ml) was added sodium hydride (60% in oil, 27 mg, 0.66 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 n-BuI (184 mg, 1.00 mmol) and N,N-dimethylformamide (1 ml) at 0° C. and stirred for 0.5 hour. After stirring at room temperature for 1 hour, 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 (4:1) to give 85 mg (62%) of the title compound as an oil.

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 1 hour
  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 (4:1)

Sources & evidence

ORD record
ord-8d701797395e49ddb383f81a1431a4cd
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Reaction notes

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