Bromoform → 2,5-Dibromo-4-methylpyrimidine
Reaction equation
C(ON=O)CC(C)C.[Br:9][C:10]1[C:11]([CH3:17])=[N:12][C:13](N)=[N:14][CH:15]=1.CCCC(C)C.C(Br)(Br)[Br:25]>>[Br:25][C:13]1[N:12]=[C:11]([CH3:17])[C:10]([Br:9])=[CH:15][N:14]=1Participants
5
Conditions
- Temperature
- 85 °C
Procedure
Isoamylnitrite (21 ml) was added to a stirred suspension of 5-bromo-4-methyl-2-pyrimidinamine (1.75 g) in bromoform (30 ml) and the mixture heated at 85° C. for 4 h. After cooling, isohexane (300 ml) was added and the solution passed through a pad of silica-gel. The silica was washed with petrol (1000 ml), dichloromethane (200 ml) then the product eluted with ethylacetate. The ethylacetate layer was evaporated under reduced pressure and the residue purified by chromatography on silica eluting with 5% diethylether/isohexane, yield 0.9 g
Workup
- temperatureAfter cooling
- washThe silica was washed with petrol (1000 ml), dichloromethane (200 ml)
- washthe product eluted with ethylacetate
- customThe ethylacetate layer was evaporated under reduced pressure
- customthe residue purified by chromatography on silica eluting with 5% diethylether/isohexane, yield 0.9 g
Sources & evidence
- ORD record
- ord-60cbfb6a2e3b4955bf8c0e02034929f5
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08158820B2
Reaction notes
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