Dimethylformamide → 3-Ethyl-5-mesityl-7-methyl-2-(propylamino)-3,7-dihydro-4h-pyrrolo[2,3-d]pyrimidin-4-one

HRID 598124Notes

Reaction equation

HRID 598124 reaction equation
[NH2:1][C:2]1[N:3]([CH2:22][CH3:23])[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+].[CH2:31](I)[CH2:32][CH3:33]>O>[CH2:22]([N:3]1[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]=[C:2]1[NH:1][CH2:31][CH2:32][CH3:33])[CH3:23]

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 24758Sodium hydrideHCID 336431-IodopropaneHCID 672679812-Amino-3-ethyl-5-mesityl-7-methyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one

Product 1

HCID 589385923-Ethyl-5-mesityl-7-methyl-2-(propylamino)-3,7-dihydro-4h-pyrrolo[2,3-d]pyrimidin-4-oneYield 27.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 2-amino-3-ethyl-5-mesityl-7-methyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one (80 mg, 0.26 mmol) and N,N-dimethylformamide (3 ml) was added sodium hydride (60% in oil, 40 mg, 1.0 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-PrI (170 mg, 1.0 mmol) and N,N-dimethylformamide (2 ml) at 0° C. and stirred for 0.5 hour. After stirring at 50° C. for 3 hours, the mixture was cooled and 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 (20:1) to give 25 mg (25%) 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 50° C. for 3 hours
  4. temperaturethe mixture was cooled
  5. extractionextracted with ethyl acetate (50 ml×2)
  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-6142a78c4713416e8c86041ebea1a4c4
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Reaction notes

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