3-Methoxyphenol → N2-(6-(3-methoxylphenoxy)pyrimidin-4-yl)pyridine-2,6-diamine

HRID 577342노트

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HRID 577342 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:19]=[C:20]([OH:24])[CH:21]=[CH:22][CH:23]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOC(C)=O>[O:17]([C:18]1[CH:19]=[C:20]([CH:21]=[CH:22][CH:23]=1)[O:24][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]

참가 물질

6

반응물 3

HCID 90073-MethoxyphenolHCID 11430Potassium CarbonateHCID 57708264N2-(6-chloropyrimidin-4-yl)pyridine-2,6-diamine

생성물 1

HCID 57708231N2-(6-(3-methoxylphenoxy)pyrimidin-4-yl)pyridine-2,6-diamine수율 40.7%

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 3-methoxyphenol (112 mg, 0.90 mmol) and anhydrous K2CO3 (186 mg, 1.353 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). It was washed with water (5 mL), brine (5 mL), dried over Na2SO4 and then concentrated under reduced pressure to give a crude product. This was further purified by column chromatography (SiO2, 60-120, hexane/EtOAc, 5/5) to give N2-(6-(3-methoxylphenoxy)pyrimidin-4-yl)pyridine-2,6-diamine (110 mg, 40.7%) 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. washIt was washed with water (5 mL), brine (5 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customto give a crude product
  8. customThis was further purified by column chromatography (SiO2, 60-120, hexane/EtOAc, 5/5)

출처 및 근거

ORD 기록
ord-ce30146ab5524a6e8a4c106d252c14d4
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040541B2

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