Potassium Carbonate → 2-[[3-[4-(2-Cyclopropylphenyl)piperazin-1-yl]propyl]methylamino]pyrimidine-4-carboxamide

HRID 373590Notes

Reaction equation

HRID 373590 reaction equation
[CH:1]1([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[N:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][NH:19][CH3:20])[CH2:12][CH2:11]2)[CH2:3][CH2:2]1.Cl[C:22]1[N:27]=[C:26]([C:28]([NH2:30])=[O:29])[CH:25]=[CH:24][N:23]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH:1]1([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[N:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][N:19]([CH3:20])[C:22]3[N:27]=[C:26]([C:28]([NH2:30])=[O:29])[CH:25]=[CH:24][N:23]=3)[CH2:12][CH2:11]2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2470282-Chloropyrimidine-4-carboxamideHCID 198106813-[4-(2-cyclopropylphenyl)piperazin-1-yl]-N-methylpropanamine

Product 1

HCID 157182992-[[3-[4-(2-Cyclopropylphenyl)piperazin-1-yl]propyl]methylamino]pyrimidine-4-carboxamideYield 60.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1.25 g (4.09 mmol) of 3-[4-(2-cyclopropylphenyl)piperazin-1-yl]-N-methylpropanamine, 150 ml of acetonitrile, 0.645 g (4.09 mmol) of 2-chloropyrimidine-4-carboxamide and 1 g of potassium carbonate are introduced into a 250-ml round bottom flask fitted with a condenser and with a calcium chloride safety tube. The mixture is heated under reflux for 6 h, is allowed to return to room temperature, is partially concentrated and water and dichloromethane are added. The organic phase is separated off, is washed with water and is dried over sodium sulphate, the solvent is evaporated off and the residue is purified by chromatography on a column of silica gel. The oily product obtained crystallises from acetonitrile and is separated off by filtration, is rinsed with diethyl ether and is dried while heated under vacuum. 0.97 g of compound are finally isolated.

Workup

  1. customfitted with a condenser and with a calcium chloride safety tube
  2. temperatureThe mixture is heated
  3. temperatureunder reflux for 6 h
  4. customto return to room temperature
  5. concentrationis partially concentrated
  6. additionwater and dichloromethane are added
  7. customThe organic phase is separated off
  8. washis washed with water
  9. dry with materialis dried over sodium sulphate
  10. customthe solvent is evaporated off
  11. customthe residue is purified by chromatography on a column of silica gel
  12. customThe oily product obtained
  13. customcrystallises from acetonitrile
  14. customis separated off by filtration
  15. washis rinsed with diethyl ether
  16. customis dried
  17. temperaturewhile heated under vacuum

Sources & evidence

ORD record
ord-63629c67d3f442c28ce40ee5ebda7c5e
Source dataset
uspto-grants-1992_11
Patent number
US05164397

Reaction notes

Loading…