Water → 5-(Benzyloxy)pyrimidin-2-amine
Reaction equation
[CH2:1]([O:8][C:9](=[CH:12]N(C)C)[CH:10]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:17][C:18]([NH2:20])=[NH:19].[H-].[Na+].O>CN1CCCC1=O>[CH2:1]([O:8][C:9]1[CH:10]=[N:19][C:18]([NH2:20])=[N:17][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
Procedure
2-(Benzyloxy)-3-(dimethylamino)acrylaldehyde (10.95 g, 53.3 mmol) was dissolved in N-methylpyrrolidone (85 mL), the solution was added with guanidine hydrochloride (15.3 g, 160 mmol), and then the mixture was added with sodium hydride (50% in oil, 15.3 g, 320 mmol) with stirring on an ice bath, and stirred on an oil bath at 80° C. for 1 hour. The reaction mixture was added with water on an ice bath to decompose excessive sodium hydride, and then extracted with ether and water, and the organic layer was washed successively with water and saturated brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:acetone=10:1→4:1→2:1→1:1), and the concentrated residue was washed with ether-hexane, and taken by filtration to obtain 5-(benzyloxy)pyrimidin-2-amine (6.99 g, 65%) as pale yellow solid.
Workup
- stirringstirred on an oil bath at 80° C. for 1 hour
- extractionextracted with ether and water
- washthe organic layer was washed successively with water and saturated brine
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated under reduced pressure
- customThe resulting residue was purified by silica gel column chromatography (hexane:acetone=10:1→4:1→2:1→1:1)
- washthe concentrated residue was washed with ether-hexane
- filtrationtaken by filtration
Sources & evidence
- ORD record
- ord-f44632f20c46475eadecb3d52efa6b77
- Source dataset
- uspto-grants-2011_09
- Patent number
- US08012989B2
Reaction notes
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