Dimethylformamide → 3-Benzyl-2-(dipropylamino)-5-mesityl-7-methyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one

HRID 598132Notes

Reaction equation

HRID 598132 reaction equation
[CH2:1]([N:4]([CH2:25][CH2:26][CH3:27])[C:5]1[NH:6][C:7](=[O:24])[C:8]2[C:13]([C:14]3[C:19]([CH3:20])=[CH:18][C:17]([CH3:21])=[CH:16][C:15]=3[CH3:22])=[CH:12][N:11]([CH3:23])[C:9]=2[N:10]=1)[CH2:2][CH3:3].CN(C)C=O.[H-].[Na+].[CH2:35](Cl)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>O>[CH2:35]([N:6]1[C:7](=[O:24])[C:8]2[C:13]([C:14]3[C:19]([CH3:20])=[CH:18][C:17]([CH3:21])=[CH:16][C:15]=3[CH3:22])=[CH:12][N:11]([CH3:23])[C:9]=2[N:10]=[C:5]1[N:4]([CH2:1][CH2:2][CH3:3])[CH2:25][CH2:26][CH3:27])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 1360006732-(dipropylamino)-5-mesityl-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-ol

Product 1

HCID 589385513-Benzyl-2-(dipropylamino)-5-mesityl-7-methyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-oneYield 17.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-(dipropylamino)-5-mesityl-7-methyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one (50 mg, 0.14 mmol) and dimethylformamide (3 ml) was added sodium hydride (60% in oil, 10 mg, 0.25 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 benzylchloride (64 mg, 0.50 mmol) and dimethylformamide (2 ml) at 0° C. and stirred for 0.5 hour. After stirring at room temperature for 1 hour, the mixture was heated at 80° C. After cooling to room temperature, the mixture was diluted with water (20 ml) and extracted with ethyl acetate (50 ml×3). 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 (20:1) to give 11 mg (17%) 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 1 hour
  4. temperatureAfter cooling to room temperature
  5. extractionextracted with ethyl acetate (50 ml×3)
  6. washwashed with brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by silica gel chromatography
  10. washeluting with hexane/ethyl acetate (20:1)

Sources & evidence

ORD record
ord-6f62236ce8e04a8ca2ea1cf3c1d6c0ee
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Reaction notes

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