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

HRID 598123Notes

Reaction equation

HRID 598123 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+].[CH2:29](I)[CH3:30]>O>[NH2:1][C:2]1[N:3]([CH2:29][CH3:30])[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 6340IodoethaneHCID 24758Sodium hydrideHCID 1364007122-Amino-5-mesityl-7-methyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one

Product 1

HCID 672679812-Amino-3-ethyl-5-mesityl-7-methyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-oneYield 55.1%

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 (88 mg, 0.31 mmol) and N,N-dimethylformamide (3 ml) was added sodium hydride (60% in oil, 16 mg, 0.40 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 ethyl iodide (62 mg, 0.40 mmol) and N,N-dimethylformamide (1 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×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 (3:1) to give 53 mg (55%) 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×3)
  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-d5c250862b5149d2ab06fc3e1f8d838a
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Reaction notes

Loading…