Potassium Carbonate → 1-(2-Methyl-pyrimidin-5-yl)-7-(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl)-hept-1-en-3-one

HRID 1827675Notes

Reaction equation

HRID 1827675 reaction equation
COP([CH2:7][C:8](=[O:23])[CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:22]=[CH:21][C:20]2[CH2:19][CH2:18][CH2:17][NH:16][C:15]=2[N:14]=1)(=O)OC.[CH:24]([C:26]1[CH:27]=[N:28][C:29]([CH3:32])=[N:30][CH:31]=1)=O.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:32][C:29]1[N:30]=[CH:31][C:26]([CH:24]=[CH:7][C:8](=[O:23])[CH2:9][CH2:10][CH2:11][CH2:12][C:13]2[CH:22]=[CH:21][C:20]3[CH2:19][CH2:18][CH2:17][NH:16][C:15]=3[N:14]=2)=[CH:27][N:28]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 31609702-Methylpyrimidine-5-carbaldehydeHCID 11267803Dimethyl (2-oxo-6-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)hexyl)phosphonate

Product 1

HCID 693708181-(2-Methyl-pyrimidin-5-yl)-7-(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl)-hept-1-en-3-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-6 (5.5 g, 16.2 mmol), 5-formyl-2-methylpyrimidine (1-6a, 1.8 g, 14.7 mmol; for preparation, see J. Heterocyclic Chem., 28, 1281 (1991)) in 40 mL DMF was added K2CO3 (4.07 g, 32 mmol). The mixture was stirred at ambient temperature for 15 hr, and concentrated to a paste. The residue was diluted with water, extracted with ethyl acetate, and dried over magnesium sulfate. Following concentration, the residue was chromatographed on silica gel (70 chloroform/25 ethyl acetate/5 methanol) to give 1-7 as a white solid.

Workup

  1. concentrationconcentrated to a paste
  2. additionThe residue was diluted with water
  3. extractionextracted with ethyl acetate
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentration
  6. customthe residue was chromatographed on silica gel (70 chloroform/25 ethyl acetate/5 methanol)

Sources & evidence

ORD record
ord-5b7a903fa0e84a46ad52165c1cb0998e
Source dataset
uspto-grants-2006_06
Patent number
US07056909B2

Reaction notes

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