4-Methoxyphenol → N2-(6-(4-methoxylphenoxy)pyrimidin-4-yl)pyridine-2,6-diamine

HRID 577344노트

반응식

HRID 577344 반응식
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([NH2:15])[N:10]=2)[CH:3]=1.[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOC(C)=O>[O:17]([C:18]1[CH:23]=[CH:22][C:21]([O:24][C:2]2[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]3[CH:14]=[CH:13][CH:12]=[C:11]([NH2:15])[N:10]=3)[CH:3]=2)=[CH:20][CH:19]=1)[CH3:16]

참가 물질

6

반응물 3

HCID 90154-MethoxyphenolHCID 11430Potassium CarbonateHCID 57708264N2-(6-chloropyrimidin-4-yl)pyridine-2,6-diamine

생성물 1

HCID 57708329N2-(6-(4-methoxylphenoxy)pyrimidin-4-yl)pyridine-2,6-diamine수율 59.2%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
100 °C

실험 절차

To a solution of N2-(6-chloropyrimidin-4-yl)pyridine-2,6-diamine (200 mg, 0.90 mmol) in dry DMF (2 mL) was added 4-methoxyphenol (168 mg, 1.3 mmol) and anhydrous K2CO3 (179 mg, 1.3 mmol). The reaction mixture was heated at 100° C. for 16 h under N2 atmosphere. It was then cooled and DMF removed under reduced pressure to give a yellowish gummy residue that was taken in EtOAc (10 mL). The solution was washed with water (5 mL) and brine (5 mL), was dried over Na2SO4 and was then concentrated under reduced pressure to get crude product. This was further purified by column chromatography (SiO2, 60-120, hexane/EtOAc, 5/5) to give N2-(6-(4-methoxylphenoxy)pyrimidin-4-yl)pyridine-2,6-diamine (160 mg, 59.2%) as a pale yellow solid.

후처리

  1. temperatureIt was then cooled
  2. customDMF removed under reduced pressure
  3. customto give a yellowish gummy residue that
  4. washThe solution was washed with water (5 mL) and brine (5 mL)
  5. dry with materialwas dried over Na2SO4
  6. concentrationwas then concentrated under reduced pressure
  7. customto get crude product
  8. customThis was further purified by column chromatography (SiO2, 60-120, hexane/EtOAc, 5/5)

출처 및 근거

ORD 기록
ord-b55897edc0ff487594a09c2fc0fd83f9
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040541B2

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