Ammonia → 5-(2-Aminopyrimidin-4-yl)-6-(3-trifluoromethylphenyl)-1H-pyrazolo[3,4-b]pyridine

HRID 42613Notes

Reaction equation

HRID 42613 reaction equation
[NH3:1].CS([C:6]1[N:11]=[C:10]([C:12]2[CH:13]=[C:14]3[CH:30]=[N:29][NH:28][C:15]3=[N:16][C:17]=2[C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=2)[CH:9]=[CH:8][N:7]=1)(=O)=O>C1COCC1>[NH2:1][C:6]1[N:11]=[C:10]([C:12]2[CH:13]=[C:14]3[CH:30]=[N:29][NH:28][C:15]3=[N:16][C:17]=2[C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=2)[CH:9]=[CH:8][N:7]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 670138055-[2-(methylsulfonyl)pyrimidin-4-yl]-6-[3-(trifluoromethyl)phenyl]-1H-pyrazolo[3,4-b]pyridine

Product 1

HCID 104283275-(2-Aminopyrimidin-4-yl)-6-(3-trifluoromethylphenyl)-1H-pyrazolo[3,4-b]pyridineYield 9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of THF (20 mL) saturated with NH3 (g) at −20° C. was added over 5-[2-(methylsulfonyl)pyrimidin-4-yl]-6-[3-(trifluoromethyl)phenyl]-1H-pyrazolo[3,4-b]pyridine (90 mg, 0.2 mmol, obtained in example 127) in a closed vessel. It was stirred at room temperature for 2 days and concentrated. The crude product obtained was purified by chromatography on silica gel using hexane-EtOAc mixtures of increasing polarity as eluent, to afford 7 mg of the title compound (yield: 9%)

Workup

  1. concentrationconcentrated
  2. customThe crude product obtained
  3. customwas purified by chromatography on silica gel
  4. temperatureof increasing polarity as eluent

Sources & evidence

ORD record
ord-4440800fa6c44e019eee9baf511b9384
Source dataset
uspto-grants-2013_09
Patent number
US08536194B2

Reaction notes

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