3-Methyl-4-((6-methylpyridin-3-yl)oxy)aniline → HCID 57597207, compound

HRID 1925998Notes

Reaction equation

HRID 1925998 reaction equation
Cl[C:2]1[C:3]2[N:10]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:9]=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[CH3:17][C:18]1[CH:19]=[C:20]([CH:22]=[CH:23][C:24]=1[O:25][C:26]1[CH:27]=[N:28][C:29]([CH3:32])=[CH:30][CH:31]=1)[NH2:21]>C(O)(C)C.C(=O)([O-])O.[Na+]>[CH3:17][C:18]1[CH:19]=[C:20]([NH:21][C:2]2[C:3]3[N:10]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:9]=[CH:8][C:4]=3[N:5]=[CH:6][N:7]=2)[CH:22]=[CH:23][C:24]=1[O:25][C:26]1[CH:27]=[N:28][C:29]([CH3:32])=[CH:30][CH:31]=1

Participants

5

Reactant 2

HCID 114244343-Methyl-4-((6-methylpyridin-3-yl)oxy)anilineHCID 86084730HCID 86084730, compound

Product 1

HCID 57597207HCID 57597207, compoundYield 86.1%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of ethyl (4-chloro-5H-pyrrolo[3,2-d]pyrimidin-5-yl)acetate (140 mg) in isopropyl alcohol (0.6 mL) was added 3-methyl-4-[(6-methylpyridin-3-yl)oxy]aniline (188 mg), and the mixture was stirred in an oil bath at a temperature of 110° C. for 2 hrs. The reaction mixture was allowed to cool to room temperature, diluted with 5% aqueous sodium hydrogen carbonate solution (20 mL) and extracted with ethyl acetate (25 mL×3). The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was subjected to silica gel column chromatography (basic silica gel, eluent:ethyl acetate/methanol=10/0→9/1). The object fraction was concentrated under reduced pressure. Diisopropyl ether was added to the residue, and the resultant precipitate was collected by filtration and dried under reduced pressure to give the title compound (210 mg) as white powder crystals.

Workup

  1. temperatureto cool to room temperature
  2. extractionextracted with ethyl acetate (25 mL×3)
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. concentrationThe object fraction was concentrated under reduced pressure
  7. additionDiisopropyl ether was added to the residue
  8. filtrationthe resultant precipitate was collected by filtration
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-b0246c869062426db9db960e1ed02fa1
Source dataset
uspto-grants-2012_05
Patent number
US08178543B2

Reaction notes

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