Methyl iodide → Tert-butyl (5-(1,3-dioxolan-2-yl)methyl-6-oxo-5,6-dihydro-1,5-naphthyridin-3-yl)(methyl)carbamate

HRID 385568Notes

Reaction equation

HRID 385568 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][N:7]1[C:16](=[O:17])[CH:15]=[CH:14][C:13]2[N:12]=[CH:11][C:10]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:9][C:8]1=2.[H-].[Na+].CI.[C:30](OCC)(=O)C>CN(C)C=O.O>[O:3]1[CH2:4][CH2:5][O:1][CH:2]1[CH2:6][N:7]1[C:16](=[O:17])[CH:15]=[CH:14][C:13]2[N:12]=[CH:11][C:10]([N:18]([CH3:30])[C:19](=[O:25])[O:20][C:21]([CH3:22])([CH3:24])[CH3:23])=[CH:9][C:8]1=2

Participants

7

Reactant 4

HCID 6328Methyl iodide2×HCID 8857Ethyl AcetateHCID 24758Sodium hydride2×HCID 57815172HCID 57815172, compound

Product 1

HCID 57815252Tert-butyl (5-(1,3-dioxolan-2-yl)methyl-6-oxo-5,6-dihydro-1,5-naphthyridin-3-yl)(methyl)carbamate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.15 g of tert-butyl (5-(1,3-dioxolan-2-yl)methyl-6-oxo-5,6-dihydro-1,5-naphthyridin-3-yl)carbamate in 2 mL of N,N-dimethylformamide, 21 mg of 60% sodium hydride and 32 μL of methyl iodide were added, and the mixture was stirred at room temperature for 2 hours 20 minutes. Thereto were further added 9 mg of 60% sodium hydride and 13 μL of methyl iodide, and the mixture was stirred at room temperature for 1 hour. Ethyl acetate and water were added to the reaction mixture, and the organic layer was separated. The organic layer was washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The resultant residue was purified by flash silica gel column chromatography using gradient elution with hexane:ethyl acetate=1:1 to 3:7 to obtain 0.13 g of tert-butyl (5-(1,3-dioxolan-2-yl)methyl-6-oxo-5,6-dihydro-1,5-naphthyridin-3-yl)(methyl)carbamate as a brown oily substance.

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hour
  2. customthe organic layer was separated
  3. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe resultant residue was purified by flash silica gel column chromatography
  7. washelution with hexane

Sources & evidence

ORD record
ord-5725cec3ff2445358564ab4695cecd8f
Source dataset
uspto-grants-2013_02
Patent number
US08367831B2

Reaction notes

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