Dichloromethane → 5-Bromo-4-trifluoromethyl-pyrimidin-2-ylamine
Reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:8]=[CH:7][N:6]=[C:5]([NH2:9])[N:4]=1.[Br:12]N1C(=O)CCC1=O.C(Cl)Cl.[OH-].[Na+]>C(Cl)(Cl)Cl>[Br:12][C:8]1[C:3]([C:2]([F:1])([F:10])[F:11])=[N:4][C:5]([NH2:9])=[N:6][CH:7]=1Participants
6
Conditions
- Temperature
- 50 °C
Procedure
4-(Trifluoromethyl)pyrimidin-2-ylamine (2 g, 12.3 mmol) was suspended in chloroform (70 ml) followed by the addition of N-bromosuccinimide (3.3 g, 18.4 mmol) and the resulting mixture was stirred at 50° C. for 5 hours and then at room temperature for 15 hours. A mixture of methylene chloride (50 ml) and 1 M sodium hydroxide (50 ml) was added, the resulting mixture was stirred, and then the organic layer was fractionated and dried over magnesium sulfate. The solvent was evaporated under reduced pressure to give the title compound (2.2 g, 75%) as a pale orange solid.
Workup
- waitat room temperature for 15 hours
- additionwas added
- stirringthe resulting mixture was stirred
- dry with materialdried over magnesium sulfate
- customThe solvent was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-80936b36fec44a06ac3461fbe61b0d47
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08309546B2
Reaction notes
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