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

HRID 929871ノート

反応式

HRID 929871 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: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]

参加物

6

反応物 3

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

生成物 1

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

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 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.

後処理

  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)

出典と根拠

ORDレコード
ord-5d7a655b5ff942e0b2b693bafabdee3f
出典データセット
uspto-grants-2016_03
特許番号
US09296704B2

反応ノート

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