Sodium borohydride → HCID 57530960, compound
Reaction equation
[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]([C:11]2[N:16]=[C:15]([O:17][CH3:18])[CH:14]=[C:13]([O:19][CH3:20])[N:12]=2)=[O:10])[C:3]=1[NH2:4].[BH4-].[Na+]>CO>[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([CH:9]([C:11]2[N:12]=[C:13]([O:19][CH3:20])[CH:14]=[C:15]([O:17][CH3:18])[N:16]=2)[OH:10])[C:3]=1[NH2:4]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 5 °C
Procedure
2-Fluoro-6-[(4,6-dimethoxypyrimidin-2-yl)carbonyl]aniline 2.68 g (9.67 mmol) was dissolved in methanol 80 ml and, after cooling it to 5° C., sodium borohydride 0.73 g (19.33 mmol) was added thereto while stirring. Then the solution was stirred at room temperature for 2 hours. The reaction solution was distilled off under reduced pressure and the obtained crystals were dissolved in water and dichloromethane. The organic layer was separated and the water layer was further extracted three times with dichloromethane. After the organic layer had been washed with water and dried, dichloromethane was distilled off under reduced pressure to obtain the objective 2-fluoro-6-[(4,6-dimethoxypyrimidin-2-yl)hydroxymethyl]aniline 2.66 g (yield 98%) as white crystals.
Workup
- stirringThen the solution was stirred at room temperature for 2 hours
- distillationThe reaction solution was distilled off under reduced pressure
- dissolutionthe obtained crystals were dissolved in water
- customThe organic layer was separated
- extractionthe water layer was further extracted three times with dichloromethane
- washAfter the organic layer had been washed with water
- customdried
- distillationdichloromethane was distilled off under reduced pressure
Sources & evidence
- ORD record
- ord-d78ddbb740764b7387a180035a53e104
- Source dataset
- uspto-grants-2009_01
- Patent number
- US07482308B2
Reaction notes
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