Hydrochloric Acid → 3-[6-(4-Phenoxyphenylamino)-pyrimidin-4-ylamino]phenylamine
Reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[CH:10]=[C:11]([NH:15]C(=O)OC(C)(C)C)[CH:12]=[CH:13][CH:14]=2)[CH:3]=1.[O:23]([C:30]1[CH:36]=[CH:35][C:33]([NH2:34])=[CH:32][CH:31]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.Cl>C(O)CCC>[NH2:15][C:11]1[CH:10]=[C:9]([NH:8][C:4]2[CH:3]=[C:2]([NH:34][C:33]3[CH:32]=[CH:31][C:30]([O:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[CH:36][CH:35]=3)[N:7]=[CH:6][N:5]=2)[CH:14]=[CH:13][CH:12]=1Participants
5
Procedure
A solution of tert-butyl 3-(6-chloropyrimidin-4-ylamino)phenylcarbamate (200 mg, 0.6 mmol), 4-phenoxyaniline (346 mg, 1.8 mmol) and concentrated HCl (45 mg, 1.2 mmol) in n-butanol (8 mL) was subjected to microwave irradiation (160° C., 20 min). The reaction mixture was quenched with NaHCO3 solution (2 mL) and extracted with EtOAc (2×10 mL). The combined EtOAc extract was washed with water (5 mL), brine (5 mL), was dried over Na2SO4 and was concentrated under reduced pressure. The residue was further purified by column chromatography (SiO2, 60-120, Chloroform/methanol, 9/1) to give N4-(3-aminophenyl)-N6-(4-phenoxyphenyl)pyrimidine-4,6-diamine (87 mg, 37.8%) as a brown solid.
Workup
- customThe reaction mixture was quenched with NaHCO3 solution (2 mL)
- extractionextracted with EtOAc (2×10 mL)
- extractionThe combined EtOAc extract
- washwas washed with water (5 mL), brine (5 mL)
- dry with materialwas dried over Na2SO4
- concentrationwas concentrated under reduced pressure
- customThe residue was further purified by column chromatography (SiO2, 60-120, Chloroform/methanol, 9/1)
Sources & evidence
- ORD record
- ord-9d8b14863c2d4178ab359693c02e2ecf
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08445498B2
Reaction notes
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