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

HRID 404817

반응식

HRID 404817 반응식
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

참가 물질

5

반응물 3

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

생성물 1

HCID 577082883-[6-(4-Phenoxyphenylamino)-pyrimidin-4-ylamino]phenylamine수율 39.3%

시약·촉매·용매 1

HCID 2631-Butanol용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-99fa4271696846318a01ce1a921770bb
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08748606B2

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