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

HRID 860056Notes

Reaction equation

HRID 860056 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-f1b358000cdc49548a23f93ecf3b9748
Source dataset
uspto-grants-2006_12
Patent number
US07153862B2

Reaction notes

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