Methyl iodide → HCID 68008466, compound

HRID 533166Notes

Reaction equation

HRID 533166 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[N:11][C:12]2[CH2:13][CH2:14][NH:15][C:16](=[O:19])[C:17]=2[CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:22]I>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[N:11][C:12]2[CH2:13][CH2:14][N:15]([CH3:22])[C:16](=[O:19])[C:17]=2[CH:18]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 68008654HCID 68008654, compound

Product 1

HCID 68008466HCID 68008466, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(Benzyloxy)-7,8-dihydro-1,6-naphthyridin-5(6H)-one (10.0 mg, 0.04 mmol) was dissolved in DMF (0.5 mL). NaH (2.0 mg, 0.08 mmol) was added into the solution and stirred at room temperature. After 30 min, MeI (5.0 μL) was added into the mixture and allowed to stir for another hour. Reaction was then quenched with H2O (2.0 mL) and extracted with EtOAc (3.0 mL×3). The organic layers were combined and concentrated to afford pure product as a white solid (9.2 mg, 87%). LC-MS (M+H)=267.1.

Workup

  1. stirringto stir for another hour
  2. customReaction
  3. customwas then quenched with H2O (2.0 mL)
  4. extractionextracted with EtOAc (3.0 mL×3)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-21f5e69481c74a9eba2013c530db0204
Source dataset
uspto-grants-2014_10
Patent number
US08853237B2

Reaction notes

Loading…