Sodium Methoxide → 5-(2-Methoxypyrimidin-4-yl)-6-(3-trifluoromethylphenyl)-1H-pyrazolo[3,4-b]pyridine

HRID 42612Notes

Reaction equation

CS([C:5]1[N:10]=[C:9]([C:11]2[CH:12]=[C:13]3[CH:29]=[N:28][NH:27][C:14]3=[N:15][C:16]=2[C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=2)[CH:8]=[CH:7][N:6]=1)(=O)=O.[CH3:30][O-:31].[Na+]>CO>[CH3:30][O:31][C:5]1[N:10]=[C:9]([C:11]2[CH:12]=[C:13]3[CH:29]=[N:28][NH:27][C:14]3=[N:15][C:16]=2[C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=2)[CH:8]=[CH:7][N:6]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 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 MeOH (5 mL) in a closed vessel, sodium methoxide (11 mg, 0.2 mmol) was added and heated to 60° C. for 24 h. Then, sodium methoxide (11 mg, 0.2 mmol) was added and it was stirred at 60° C. for 2 h more. It was allowed to cool and was concentrated. EtOAc and buffer (pH=5.3) were added. The phases were separated and the organic phase was washed with water, dried over Na2SO4 and concentrated to dryness. The crude product obtained was purified by chromatography on silica gel using hexane-EtOAc mixtures at 50%, to afford 38 mg of the title compound (yield: 47%)

Workup

temperatureto cool
concentrationwas concentrated
additionEtOAc and buffer (pH=5.3) were added
customThe phases were separated
washthe organic phase was washed with water
dry with materialdried over Na2SO4
concentrationconcentrated to dryness
customThe crude product obtained
customwas purified by chromatography on silica gel

Sources & evidence

ORD record: ord-61529c28765944fdbe3723d3d5df6ba4
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08536194B2

Reaction notes

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