Potassium Carbonate → HCID 135780265, compound

HRID 1296431Notes

Reaction equation

HRID 1296431 reaction equation
Cl.Cl.[N:3]1[CH:8]=[CH:7][C:6]([CH:9]2[NH:14][C:13]([NH2:15])=[N:12][CH2:11][CH2:10]2)=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].[N:22]1[CH:27]=[CH:26][C:25]([C:28](=O)[CH2:29][C:30]([O:32]CC)=O)=[CH:24][CH:23]=1>C(O)C>[N:22]1[CH:23]=[CH:24][C:25]([C:28]2[N:15]=[C:13]3[NH:14][CH:9]([C:6]4[CH:7]=[CH:8][N:3]=[CH:4][CH:5]=4)[CH2:10][CH2:11][N:12]3[C:30](=[O:32])[CH:29]=2)=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2735202Ethyl 3-(4-pyridyl)-3-oxopropionateHCID 23026173HCID 23026173, compound

Product 1

HCID 135780265HCID 135780265, compoundYield 21.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension containing 1.0 g (4.01 mmoles) of 6-(4-pyridinyl)-1,4,5,6-tetrahydro-2-pyrimidinamine dihydrochloride in 30 ml of ethanol was treated with 1.94 g (14.05 mmoles) of potassium carbonate and allowed to stir for 5 min. 1.0 g (4.01 mmoles) of ethyl 3-(pyridin-4-yl)-3-oxopropionate were added and the resulting mixture was heated at reflux temperature for 18 h. The cooled solution was evaporated to remove solvent and the residue was dissolved in water and extracted with dichloromethane. The organic extracts were washed with a saturated solution of aqueous sodium chloride, dried and the solvent evaporated under reduced pressure. The crude product thus obtained was purified using silica gel chromatography eluting with a gradient of dichloromethane/methanol/concentrated aqueous ammonia solution in the proportions 95/5/0.5 to 80/20/2. 0.26 g (21%) of pure product was obtained. Mp: 268-270° C.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux temperature for 18 h
  3. customThe cooled solution was evaporated
  4. customto remove solvent
  5. dissolutionthe residue was dissolved in water
  6. extractionextracted with dichloromethane
  7. washThe organic extracts were washed with a saturated solution of aqueous sodium chloride
  8. customdried
  9. customthe solvent evaporated under reduced pressure
  10. customThe crude product thus obtained
  11. customwas purified
  12. washeluting with a gradient of dichloromethane/methanol/concentrated aqueous ammonia solution in the proportions 95/5/0.5 to 80/20/2

Sources & evidence

ORD record
ord-60cbc5766e1146b7bc4b05ceb8ca210a
Source dataset
uspto-grants-2007_07
Patent number
US07247638B2

Reaction notes

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