Trifluoroacetic acid → 5-Fluoro-6-methoxypyridin-3-amine
Reaction equation
C(O)(C(F)(F)F)=O.[F:8][C:9]1[CH:10]=[C:11]([NH:17]C(=O)OC(C)(C)C)[CH:12]=[N:13][C:14]=1[O:15][CH3:16]>>[F:8][C:9]1[CH:10]=[C:11]([NH2:17])[CH:12]=[N:13][C:14]=1[O:15][CH3:16]Participants
3
Procedure
TFA (2 ml) was added to tert-butyl (5-fluoro-6-methoxypyridin-3-yl)carbamate (279 mg) obtained in the 1st step, followed by stirring at room temperature for 1 hour. The solvent was distilled away under reduced pressure and a 5M sodium hydroxide aqueous solution was added to the obtained residue at 0° C. so as to alkalify the mixture, followed by extraction with ethyl acetate. The organic layers were washed with saturated saline and dried over anhydrous sodium sulfate and the solvent was distilled away under reduced pressure. A light brown solid of 5-fluoro-6-methoxypyridin-3-amine (19 mg) was thus obtained.
Workup
- customobtained in the 1st step
- distillationThe solvent was distilled away under reduced pressure
- additiona 5M sodium hydroxide aqueous solution was added to the obtained residue at 0° C. so as
- extractionfollowed by extraction with ethyl acetate
- washThe organic layers were washed with saturated saline
- dry with materialdried over anhydrous sodium sulfate
- distillationthe solvent was distilled away under reduced pressure
Sources & evidence
- ORD record
- ord-13ba9d3b2d9846ecbc3e2d54e22544f8
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09051310B2
Reaction notes
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