Hydrochloric Acid → 3-[6-(4-Phenoxyphenylamino)-pyrimidin-4-ylamino]phenylamine

HRID 404817

Reaktionsgleichung

Reaktionsgleichung von HRID 404817
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]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 8764(4-Aminophenoxy)benzeneHCID 57708283Tert-butyl 3-(6-chloropyrimidin-4-ylamino)phenylcarbamate

Produkt 1

HCID 577082883-[6-(4-Phenoxyphenylamino)-pyrimidin-4-ylamino]phenylamineAusbeute 39,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2631-ButanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  1. customThe reaction mixture was quenched with NaHCO3 solution (2 mL)
  2. extractionextracted with EtOAc (2×10 mL)
  3. extractionThe combined EtOAc extract
  4. washwas washed with water (5 mL), brine (5 mL)
  5. dry with materialwas dried over Na2SO4
  6. concentrationwas concentrated under reduced pressure
  7. customThe residue was further purified by column chromatography (SiO2, 60-120, Chloroform/methanol, 9/1)

Quellen und Nachweise

ORD-Eintrag
ord-99fa4271696846318a01ce1a921770bb
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08748606B2

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