Hydrochloric Acid → 5-Bromo-N-(propan-2-yl)pyridin-2-amine
Reaction equation
[Br:1][C:2]1[CH:3]=N[C:5](Cl)=[N:6][CH:7]=1.[CH:9]([NH2:12])([CH3:11])[CH3:10].Cl.[CH2:14]1COCC1>>[Br:1][C:2]1[CH:3]=[CH:14][C:5]([NH:12][CH:9]([CH3:11])[CH3:10])=[N:6][CH:7]=1Participants
5
Conditions
- Temperature
- 65 °C
Procedure
To a solution of 5-bromo-2-chloropyrimidine (600 mg) in THF (10 mL) was added isopropylamine (5.30 mL) and the reaction heated at 65° C. for 16 h. After cooling to room temperature the mixture was poured into 2 M aqueous HCl (30 mL) and washed with dichloromethane (30 mL). The aqueous layer was made basic with sodium carbonate and the product extracted into dichloromethane (3×20 mL). The organic layers were dried (MgSO4) and reduced in vacuo to give (5-bromo-pyridin-2-yl)-isopropylamine as an off-white solid.
Workup
- temperatureAfter cooling to room temperature the mixture
- washwashed with dichloromethane (30 mL)
- extractionthe product extracted into dichloromethane (3×20 mL)
- dry with materialThe organic layers were dried (MgSO4)
Sources & evidence
- ORD record
- ord-06f645f0eff7477984fd9c7d07502e96
- Source dataset
- uspto-grants-2011_02
- Patent number
- US07888352B2
Reaction notes
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