Trifluoroacetic acid → HCID 178510667, compound

HRID 487287Notes

Reaction equation

HRID 487287 reaction equation
[CH:1]1([N:6]2[C:10]3=[N:11][C:12]([C:16]4[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=4)=[N:13][C:14](N)=[C:9]3[C:8]([C:22]#[N:23])=[N:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.FC(F)(F)C(O)=[O:27].N([O-])=O.[Na+].[OH-].[NH4+]>C(O)(=O)C.O>[CH:1]1([N:6]2[C:10]3=[N:11][C:12]([C:16]4[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=4)=[N:13][C:14](=[O:27])[C:9]3=[C:8]([C:22]#[N:23])[NH:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 14923Ammonium HydroxideHCID 19432788HCID 19432788, compoundHCID 23668193Sodium Nitrite2×

Product 1

HCID 178510667HCID 178510667, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent2×

Procedure

To a solution of 1-cyclopentyl-3-cyano-6-(4-pyridyl)pyrazolo(3,4-d)pyrimidin-4-amine (0.61 g, 2.0 mmol) in 50% acetic acid (70 ml) at -5° to 0° C. was added 50% trifluoroacetic acid (10 ml) followed by sodium nitrite (2.8 g, 40.6 mmol) in water (15 ml). The reaction mixture was stirred at -5° to 0° C. for 1 hour, then at room temperature for 3 hours. The reaction mixture was cooled back to -5° to 0° C. and sodium nitrite (1.4 g, 20.3 mmol) in water (5 ml) was added. The reaction mixture was warmed to room temperature and stirred for 3 hours. The mixture was poured onto ice-water, concentrated ammonium hydroxide was added, followed by acetic acid to adjust the pH to 5. The product was collected by filtration, washed with water and recrystallized from ethanol to afford 0.48 g (79%) of 1-cyclopentyl-3-cyano-6-(4-pyridyl)pyrazolo[3,4-d]pyrimidin-4-one as a white fluffy powder, m.p. >300° C. when dried at 110° C. for 96 hours in high vacuum.

Workup

  1. waitat room temperature for 3 hours
  2. temperatureThe reaction mixture was cooled back to -5° to 0° C.
  3. stirringstirred for 3 hours
  4. additionwas added
  5. filtrationThe product was collected by filtration
  6. washwashed with water
  7. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-516110f374ca440294014500d1cf1a02
Source dataset
uspto-grants-1994_03
Patent number
US05294612

Reaction notes

Loading…