Trifluoroacetic acid → HCID 178510667, compound

HRID 1736577Notes

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

Conditions

Temperature: -2.5 °C

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

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

Sources & evidence

ORD record: ord-e55e4aae3bb14d51a3ba20d5f9d13ca0
Source dataset: uspto-grants-1996_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05541187

Reaction notes

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