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

HRID 404817ノート

反応式

HRID 404817 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 2631-Butanol溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-99fa4271696846318a01ce1a921770bb
出典データセット
uspto-grants-2014_06
特許番号
US08748606B2

反応ノート

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