Methyl iodide → Ethyl 1,6,8-Trimethyl-4-oxo-1,4-dihydro-1,7-naphthyridine-3-carboxylate

HRID 411229

Reaction equation

HRID 411229 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[C:7]([CH3:13])[N:8]=[C:9]([CH3:12])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15].[C:19]([O-])([O-])=O.[Na+].[Na+].IC>CN(C=O)C>[CH3:19][N:5]1[C:6]2[C:11](=[CH:10][C:9]([CH3:12])=[N:8][C:7]=2[CH3:13])[C:2](=[O:1])[C:3]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:4]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10340Sodium CarbonateHCID 22397159Ethyl 4-Hydroxy-6,8-dimethyl-1,7-naphthyridine-3-carboxylate

Product 1

HCID 22397181Ethyl 1,6,8-Trimethyl-4-oxo-1,4-dihydro-1,7-naphthyridine-3-carboxylateYield 21%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl 4-hydroxy-6,8-dimethyl-1,7-naphthyridine-3-carboxylate (Preparation 47, 460 mg) is dissolved in DMF (30 mL) and treated with Na2CO3 (396 mg). Iodomethane (0.3 mL) is slowly added to the mixture, and it is then heated to reflux for 1 h. The reaction mixture is cooled to room temperature, quenched with water (20 mL) and extracted with CH2Cl2 (50 mL). The organic layer is separated, dried (MgSO4), and concentrated in vacuo. The residue is purified by silica gel column chromatography (5% methanol/CH2Cl2) to give 100 mg (21%) of the title compound as a white solid. Physical characteristics: MS (ESI+) m/z 261 (M+H)+; 1H NMR (DMSO) δ 8.61, 7.78, 4.23, 4.18, 3.00, 2.56, 1.28.

Workup

  1. temperatureis then heated
  2. temperatureto reflux for 1 h
  3. customquenched with water (20 mL)
  4. extractionextracted with CH2Cl2 (50 mL)
  5. customThe organic layer is separated
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customThe residue is purified by silica gel column chromatography (5% methanol/CH2Cl2)

Sources & evidence

ORD record
ord-8a9eac3c2e3c488289e7de5278ae5083
Source dataset
uspto-grants-2003_05
Patent number
US06559145B2

Linked notes

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