Water → 2-(Dimethylamino)-5-mesityl-3,7-dimethyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one
Reaction equation
N[C:2]1[NH:3][C:4](=O)[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.[CH3:22][N:23]([CH3:26])[CH:24]=O.[H-].[Na+].CI.[OH2:31]>>[CH3:22][N:23]([CH3:26])[C:24]1[N:3]([CH3:2])[C:4](=[O:31])[C:5]2[C:10]([C:11]3[C:12]([CH3:19])=[CH:13][C:14]([CH3:18])=[CH:15][C:16]=3[CH3:17])=[CH:9][N:8]([CH3:20])[C:6]=2[N:7]=1Participants
Procedure
To a solution of 2-amino-5-mesityl-7-methyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one (115 mg, 0.41 mmol) and N,N-dimethylformamide (3 ml) was added sodium hydride (60% in oil, 52 mg, 1.30 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 MeI (213 mg, 1.50 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 110 mg (83%) of the title compound.
Workup
- stirringAfter stirring at room temperature for 0.5 hour, to the mixture
- stirringstirred for 0.5 hour
- stirringAfter stirring at room temperature for 1 hour
- extractionextracted with ethyl acetate (50 ml×2)
- washwashed with brine
- dry with materialdried over sodium sulfate
- concentrationconcentrated in vacuo
- customThe residue was purified by silica gel chromatography
- washeluting with hexane/ethyl acetate (4:1)
Sources & evidence
- ORD record
- ord-f1a287a2bc464466a4fd2c08d6557d7a
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07897607B2
Reaction notes
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