Acetic Acid → 1-(2-Fluorobenzyl)-1H-pyrazolo[3,4-d]pyrimidine-3-carboximidamide acetate

HRID 570540Notes

Reaction equation

HRID 570540 reaction equation
[F:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][CH:11]=[N:12][CH:13]=[C:8]2[C:7]([C:14]#[N:15])=[N:6]1.C[O-].[Na+].[C:23]([OH:26])(=[O:25])[CH3:24].[Cl-].[NH4+:28]>CO>[C:23]([OH:26])(=[O:25])[CH3:24].[F:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][CH:11]=[N:12][CH:13]=[C:8]2[C:7]([C:14](=[NH:28])[NH2:15])=[N:6]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 25517Ammonium ChlorideHCID 10942334Sodium MethoxideHCID 866921051-(2-Fluorobenzyl)-1H-pyrazolo[3,4-d]pyrimidine-3-carbonitrile

Product 1

HCID 866921061-(2-Fluorobenzyl)-1H-pyrazolo[3,4-d]pyrimidine-3-carboximidamide acetate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Under an argon atmosphere, 685 mg (purity 84%, approx. 2.273 mmol) of 1-(2-fluorobenzyl)-1H-pyrazolo[3,4-d]pyrimidine-3-carbonitrile were dissolved in 8 ml of absolute methanol. 127 mg (2.273 mmol) of sodium methoxide were added and the mixture was stirred at RT for 1 h. 532 mg (8.864 mmol) of acetic acid and 299 mg (2.273 mmol) of ammonium chloride were added and the mixture was boiled under reflux for 45 min. The reaction mixture was concentrated, the residue was stirred with 20 ml of 1N sodium hydroxide solution, and the precipitate was filtered off with suction and dried under high vacuum. 610 mg (purity 86%, 86% of theory) of the target compound were obtained.

Workup

  1. temperatureunder reflux for 45 min
  2. concentrationThe reaction mixture was concentrated
  3. stirringthe residue was stirred with 20 ml of 1N sodium hydroxide solution
  4. filtrationthe precipitate was filtered off with suction
  5. customdried under high vacuum
  6. custom610 mg (purity 86%, 86% of theory) of the target compound were obtained

Sources & evidence

ORD record
ord-6c36462450bb430abfca5b1f07b71e43
Source dataset
uspto-grants-2015_05
Patent number
US09023849B2

Reaction notes

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