M-Cresol → 2-[6-(3-Methylphenoxy)-pyrimidin-4-yl]amino-6-aminopyridine

HRID 929842ノート

反応式

HRID 929842 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][C:17]1[CH:18]=[C:19]([OH:23])[CH:20]=[CH:21][CH:22]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOC(C)=O>[CH3:16][C:17]1[CH:18]=[C:19]([CH:20]=[CH:21][CH:22]=1)[O:23][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

参加物

6

反応物 3

HCID 342M-CresolHCID 11430Potassium CarbonateHCID 57708264N2-(6-chloropyrimidin-4-yl)pyridine-2,6-diamine

生成物 1

HCID 577083532-[6-(3-Methylphenoxy)-pyrimidin-4-yl]amino-6-aminopyridine収率 75.8%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
145 °C

実験手順

To a solution of N2-(6-chloropyrimidin-4-yl)pyridine-2,6-diamine (100 mg, 0.45 mmol) in DMF (1 mL) was added 3-methylphenol (88 mg, 0.8 mmol) and anhydrous K2CO3 (93 mg, 0.6 mmol). The reaction mixture was heated at 145° C. for 16 h. It was then cooled and DMF was removed under reduced pressure to get a yellow gummy residue. The residue was taken in EtOAc (20 mL) and washed with water (5 mL), brine (5 mL) and dried over Na2SO4. Filtration followed by concentration under reduced pressure afforded a yellow gum which was further purified by column chromatography (SiO2, 60-120, EtOAc/hexane, 5/5) to give N2-(6-(3-methylphenoxy) pyrimidin-4-yl)pyridine-2,6-diamine (IR-12) (100 mg, 75%) as a pale yellow solid.

後処理

  1. temperatureIt was then cooled
  2. customDMF was removed under reduced pressure
  3. customto get a yellow gummy residue
  4. washwashed with water (5 mL), brine (5 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationFiltration
  7. concentrationfollowed by concentration under reduced pressure
  8. customafforded a yellow gum which
  9. customwas further purified by column chromatography (SiO2, 60-120, EtOAc/hexane, 5/5)

出典と根拠

ORDレコード
ord-6a6d437591bb45fc95694676b180f212
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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