Potassium Carbonate → 7-[6-(4-Methoxy-benzylamino)-pyridin-2-yl]-1-pyrimidin-4-yl-hept-1-en-3-one

HRID 2120667Notes

Reaction equation

HRID 2120667 reaction equation
COP([CH2:7][C:8](=[O:29])[CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([NH:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)[N:14]=1)(=O)OC.[N:30]1[CH:35]=[C:34](C=O)[CH:33]=[N:32][CH:31]=1.[C:38]([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:28][O:27][C:24]1[CH:23]=[CH:22][C:21]([CH2:20][NH:19][C:15]2[N:14]=[C:13]([CH2:12][CH2:11][CH2:10][CH2:9][C:8](=[O:29])[CH:7]=[CH:38][C:35]3[CH:34]=[CH:33][N:32]=[CH:31][N:30]=3)[CH:18]=[CH:17][CH:16]=2)=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2761034Pyrimidine-5-carboxaldehydeHCID 58765549{6-[6-(4-Methoxy-benzylamino)-pyridin-2-yl]-2-oxo-hexyl}-phosphonic acid dimethyl ester

Product 1

HCID 696676747-[6-(4-Methoxy-benzylamino)-pyridin-2-yl]-1-pyrimidin-4-yl-hept-1-en-3-oneYield 80.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-7 (1.87 g, 4.44 mmol), pyrimidine-5-carbaldehyde (0.480 g, 4.44 mmol) in 15 mL DMF was added K2CO3 (0.922 g, 6.67 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 sodium sulfate. Following concentration, the residue was chromatographed on silica gel (5% MeOH/CH2Cl2) to give 1.44 g of 6-8 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 sodium sulfate
  5. concentrationconcentration
  6. customthe residue was chromatographed on silica gel (5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-7b9271d856824721b53c461003346d8f
Source dataset
uspto-grants-2004_02
Patent number
US06693101B2

Reaction notes

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