Water → N-(6-(4-Nitrophenoxy)pyrimidin-4-yl)phenylamine
Reaction equation
Cl[C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=2)[N:5]=[CH:4][N:3]=1.[NH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(OCC)(=O)C.O>CN1CCCC1=O.CCCCCC>[N+:15]([C:12]1[CH:13]=[CH:14][C:9]([O:8][C:6]2[N:5]=[CH:4][N:3]=[C:2]([NH:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:7]=2)=[CH:10][CH:11]=1)([O-:17])=[O:16]Participants
7
Procedure
4-Chloro-6-(4-nitrophenoxy)pyrimidine (508 mg, 2.00 mmol) and aniline (559 mg, 6.00 mmol) were heated and stirred in 1-methylpyrrolidone (5 ml) at 90° C. for 3 hours. The reaction solution was distributed between ethyl acetate and water, the organic layer was washed with water and saturated brine and dried over anhydrous magnesium sulfate, the drying agent was filtered off and the filtrate was distilled off under reduced pressure. The obtained crude product was subjected to silica gel column chromatography (eluent—ethyl acetate:hexane=1:3), and the fraction containing the target substance was concentrated to obtain the title compound (508 mg, 1.65 mmol, 82%) as colorless crystals.
Workup
- washthe organic layer was washed with water and saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- filtrationthe drying agent was filtered off
- distillationthe filtrate was distilled off under reduced pressure
- customThe obtained crude product
- additionthe fraction containing the target substance
- concentrationwas concentrated
Sources & evidence
- ORD record
- ord-14c4d8b5010247ce92ea6013580a1217
- Source dataset
- uspto-grants-2011_07
- Patent number
- US07973160B2
Reaction notes
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