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

HRID 404813ノート

反応式

HRID 404813 の反応式
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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-085fc37d00d94cbab6701e9d978d0e48
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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