Tetrafluoroboric acid → HCID 178481919, compound

HRID 72703Notes

Reaction equation

HRID 72703 reaction equation
[CH3:1][N:2]1[C:6]2=[N:7][CH:8]=[N:9][C:10]([OH:11])=[C:5]2[CH:4]=[N:3]1.[I:12]N1C(=O)CCC1=O.F[B-](F)(F)F.[H+].C(=O)(O)[O-].[Na+]>C(#N)C.O>[I:12][C:4]1[C:5]2[C:6](=[N:7][CH:8]=[N:9][C:10]=2[OH:11])[N:2]([CH3:1])[N:3]=1

Participants

7

Reactant 4

HCID 28118Tetrafluoroboric acidHCID 120273N-IodosuccinimideHCID 516892Sodium BicarbonateHCID 178481767HCID 178481767, compound

Product 1

HCID 178481919HCID 178481919, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

1-Methyl-1H-pyrazolo[3,4-d]pyrimidin-4-ol (5.50 g, 36.6 mmol) was combined with N-iodosuccinimide (97%, 12.7 g, 54.8 mmol) and tetrafluoroboric acid (50% solution in water, 23.0 mL, 183 mmol) in acetonitrile (50 mL) and the reaction mixture was heated to reflux for 5 hours. After cooling to room temperature, the reaction mixture was poured portion-wise into water (50 mL) containing sodium bicarbonate (18.6 g, 220 mmol). When gas evolution had ceased, the mixture was filtered, and the dark solid was washed successively with saturated aqueous sodium thiosulfate solution (25 mL) and water (2×25 mL). The resulting solid was dried under vacuum overnight at 50° C. to afford the product as a cream-colored solid. Yield: 9.35 g, 33.9 mmol, 93%. LCMS m/z 277.0 (M+1). 1H NMR (500 MHz, DMSO-d6) δ 3.87 (s, 3H), 8.07 (s, 1H), 12.08 (v br s, 1H).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 5 hours
  3. filtrationthe mixture was filtered
  4. washthe dark solid was washed successively with saturated aqueous sodium thiosulfate solution (25 mL) and water (2×25 mL)
  5. customThe resulting solid was dried under vacuum overnight at 50° C.

Sources & evidence

ORD record
ord-66b0366bb8ec4ba5989d196a35c4a5eb
Source dataset
uspto-grants-2014_09
Patent number
US08829010B2

Reaction notes

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