Formamide → 1-(3,5-dimethylphenyl)-1H,4H,5H-pyrazolo[3,4-d]pyrimidin-4-one

HRID 1801686Notes

Reaction equation

HRID 1801686 reaction equation
[CH:1](N)=O.[NH2:4][C:5]1[N:9]([C:10]2[CH:15]=[C:14]([CH3:16])[CH:13]=[C:12]([CH3:17])[CH:11]=2)[N:8]=[CH:7][C:6]=1[C:18]([NH2:20])=[O:19]>O>[CH3:16][C:14]1[CH:15]=[C:10]([N:9]2[C:5]3[N:4]=[CH:1][NH:20][C:18](=[O:19])[C:6]=3[CH:7]=[N:8]2)[CH:11]=[C:12]([CH3:17])[CH:13]=1

Participants

4

Reactant 2

HCID 713FormamideHCID 247958345-amino-1-(3,5-dimethylphenyl)-1H-pyrazole-4-carboxamide

Product 1

HCID 1355447751-(3,5-dimethylphenyl)-1H,4H,5H-pyrazolo[3,4-d]pyrimidin-4-oneYield 69.21%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
190 °C

Procedure

Charged 300.0 g of formamide into a 2.0 L 4 necked round bottom flask connected to a mechanical stirrer, thermo meter socket, and condenser under nitrogen atmosphere. 90.0 g (0.39 mol) of 5-Amino-1-(3,5-dimethyl-phenyl)-1H-pyrazole-4-carboxylic acid amide (Compound No. 77) was charged. Reaction mass temperature was raised to reflux (185-195° C.). Maintained the mass temperature at reflux for 60-90 min. Reaction mass temperature was cooled to 140-150° C. 900.0 ml of water was added slowly at maintaining the mass temperature 80-150° C. Maintained the mass temperature at 80-90° C. for 45-60 min. Reaction mass temperature was cooled to 25-30° C. Maintained the mass temperature at 25-30° C. for 90-120 min. Solid was filtered and solid was washed with 150.0 ml of water. 500.0 ml of DM Water and wet crude compound were charged into a 2.0 L 4 necked round bottom flask connected to a mechanical stirrer, thermo meter socket, and condenser. Mass temperature was raised to reflux. Maintained the mass temperature at reflux for 75-90 min and mass temperature was cooled to 25-30° C. Maintained the mass temperature at 25-30° C. for 90-120 min. Solid was filtered and solid was washed with 100.0 ml of water. Compound was dried under vacuum at 60-65° C. Dry weight of the compound: 65.0 g (yield 69.21%)

Workup

  1. customconnected to a mechanical stirrer
  2. addition77) was charged
  3. customReaction mass temperature
  4. temperaturewas raised
  5. temperatureMaintained the mass temperature
  6. temperatureat reflux for 60-90 min
  7. customReaction mass temperature
  8. temperaturewas cooled to 140-150° C
  9. temperatureat maintaining the mass temperature 80-150° C
  10. temperatureMaintained the mass temperature at 80-90° C. for 45-60 min
  11. customReaction mass temperature
  12. temperaturewas cooled to 25-30° C
  13. temperatureMaintained the mass temperature at 25-30° C. for 90-120 min
  14. filtrationSolid was filtered
  15. washsolid was washed with 150.0 ml of water
  16. addition500.0 ml of DM Water and wet crude compound were charged into a 2.0 L 4 necked round bottom flask
  17. customconnected to a mechanical stirrer
  18. temperatureMass temperature was raised
  19. temperatureto reflux
  20. temperatureMaintained the mass temperature
  21. temperatureat reflux for 75-90 min
  22. temperaturemass temperature was cooled to 25-30° C
  23. temperatureMaintained the mass temperature at 25-30° C. for 90-120 min
  24. filtrationSolid was filtered
  25. washsolid was washed with 100.0 ml of water
  26. customCompound was dried under vacuum at 60-65° C
  27. customDry weight of the compound

Sources & evidence

ORD record
ord-f23fc7207e09436790bf364465f716a7
Source dataset
uspto-grants-2013_01
Patent number
US08349847B2

Reaction notes

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