Ethanol → [1-(3,5-Dimethyl-phenyl)-1H-pyrazolo[3,4-d]pyrimidine-4-yl]-[2-(2-methoxy-ethoxy)-ethyl]-amine

HRID 1801685

Reaction equation

HRID 1801685 reaction equation
C(O)C.Cl[C:5]1[N:10]=[CH:9][N:8]=[C:7]2[N:11]([C:14]3[CH:19]=[C:18]([CH3:20])[CH:17]=[C:16]([CH3:21])[CH:15]=3)[N:12]=[CH:13][C:6]=12.[CH3:22][O:23][CH2:24][CH2:25][O:26][CH2:27][CH2:28][NH2:29].C(OC(C)C)(C)C>C(#N)C>[CH3:21][C:16]1[CH:15]=[C:14]([N:11]2[C:7]3=[N:8][CH:9]=[N:10][C:5]([NH:29][CH2:28][CH2:27][O:26][CH2:25][CH2:24][O:23][CH3:22])=[C:6]3[CH:13]=[N:12]2)[CH:19]=[C:18]([CH3:20])[CH:17]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 7914Diisopropyl EtherHCID 5205302-(2-Methoxyethoxy)ethanamineHCID 49621194-chloro-1-(3,5-dimethylphenyl)-1H-pyrazolo[3,4-d]pyrimidine

Product 1

HCID 44182509[1-(3,5-Dimethyl-phenyl)-1H-pyrazolo[3,4-d]pyrimidine-4-yl]-[2-(2-methoxy-ethoxy)-ethyl]-amineYield 56.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
27.5 °C

Procedure

60.0 ml of ethanol and 10.0 g (0.038 mol) of 4-chloro-1-(3,5-dimethyl-phenyl)-1H-pyrazolo[3,4-d]pyrimidine (Compound No. 79) were charged into a 250 ml of 4 necked round bottom flask connected to a mechanical stirrer, thermometer socket, condenser and addition funnel. 22.40 g (0.18 mol) of 2-(2-Methoxy-ethoxy)-ethyl amine was charged at 25-30° C. under stirring. Reaction mass temperature was raised to reflux. Maintained the mass temperature at reflux for 5 hours. Reaction mass temperature was cooled to 25-30° C. Maintained the mass temperature at 25-30° C. for 60 min. Reaction mass temperature cooled to 0-5° C. Maintained the mass temperature at 0-5° C. for 60 min. Solid does not formed. Distilled off Ethanol completely under vacuum. Crude oily mass was obtained. Oily mass was dissolved in 45 ml of acetonitrile. 300.0 ml of isopropyl ether was added. Solid was formed. Solid was filtered and solid was washed with 50.0 ml of isopropyl ether. Compound was dried under vacuum at 60-65° C. Dry weight of the compound: 7.50 g (yield—56.80%). Melting point: 90.4° C.

Workup

  1. customconnected to a mechanical stirrer
  2. additionthermometer socket, condenser and addition funnel
  3. customReaction mass temperature
  4. temperaturewas raised
  5. temperatureto reflux
  6. temperatureMaintained the mass temperature
  7. temperatureat reflux for 5 hours
  8. customReaction mass temperature
  9. temperatureMaintained the mass temperature at 25-30° C. for 60 min
  10. customReaction mass temperature
  11. temperaturecooled to 0-5° C
  12. temperatureMaintained the mass temperature at 0-5° C. for 60 min
  13. customSolid does not formed
  14. distillationDistilled off Ethanol completely under vacuum
  15. customCrude oily mass was obtained
  16. customSolid was formed
  17. filtrationSolid was filtered
  18. washsolid was washed with 50.0 ml of isopropyl ether
  19. customCompound was dried under vacuum at 60-65° C
  20. customDry weight of the compound

Sources & evidence

ORD record
ord-cd83a7dbadbf4b988373792400e9f065
Source dataset
uspto-grants-2013_01
Patent number
US08349847B2

Linked notes

Loading…