Triethylamine → HCID 59527231, compound

HRID 384482Notes

Reaction equation

HRID 384482 reaction equation
[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=[C:11]([CH2:19][O:20][C:21]2[N:26]=[CH:25][C:24](Br)=[CH:23][N:22]=2)[C:10]=1[CH3:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN([CH:32]=[O:33])C.[CH3:34][OH:35].C(N(CC)CC)C>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=[C:11]([CH2:19][O:20][C:21]2[N:26]=[CH:25][C:24]([C:34]([O:33][CH3:32])=[O:35])=[CH:23][N:22]=2)[C:10]=1[CH3:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 21901440N,N-dimethylformamide methanolHCID 59527451HCID 59527451, compound

Product 1

HCID 59527231HCID 59527231, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

4-(Benzyloxy)-2-{[(5-bromopyrimidin-2-yl)oxy]methyl}-3-methylquinoline (1.5 g) was suspended in a mixed solvent (40 mL) of DMF-methanol (1:1), and triethylamine (1 mL) and dichlorobis(triphenylphosphine)palladium(II) (1.2 g) were added thereto, followed by stirring at 100° C. under a carbon monoxide atmosphere (1.0 MPa) for 5 hours. The reaction mixture was allowed to cool to room temperature, and water was added thereto, followed by extraction with ethyl acetate. The organic layer was washed water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and then the residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=100/0˜50/50). The solvent was evaporated under reduced pressure, and ethyl acetate was added to the residue which was then warmed to be dissolved. Hexane was added to this solution, followed by stirring at room temperature, and the resulting solid was collected by filtration and dried under vacuum at room temperature to obtain 1.034 g of methyl 2-{[4-(benzyloxy)-3-methylquinolin-2-yl]methoxy}pyrimidine-5-carboxylate as a pale yellow solid.

Workup

  1. additionwere added
  2. temperatureto cool to room temperature
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=100/0˜50/50)
  8. customThe solvent was evaporated under reduced pressure, and ethyl acetate
  9. additionwas added to the residue which
  10. temperaturewas then warmed
  11. dissolutionto be dissolved
  12. additionHexane was added to this solution
  13. stirringby stirring at room temperature
  14. filtrationthe resulting solid was collected by filtration
  15. customdried under vacuum at room temperature

Sources & evidence

ORD record
ord-c43e1e8248124697b8ef9ee82823eaa0
Source dataset
uspto-grants-2013_02
Patent number
US08367702B2

Reaction notes

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