3-Methyl-1H-pyrazolo[3,4-b]pyridine-5-amine synthesis

Yield: 92%

Reaction Conditions:

with hydrogen;palladium 10% on activated carbon in ethanol for 4.25 h;

Steps:

4.B
A 25 mL round bottom flask was charged with 3-methyl-5-nitro-lH- pyrazolo[3,4-b]pyridine (39 mg, 0.22 mmol) and 10% (wt.) Pd on activated carbon (12 mg, 0.011 mmol). EtOH (10 mL) was added, and then H₂ was passed through the reaction mixture for 15 minutes. The vessel was left to stir under an H₂ balloon for 4 hours, after which it was filtered through a 0.45 μm PVDF filter. The volatiles were removed to afford 3- methyl-lH-pyrazolo[3,4-b]pyridin-5-amine as a solid (30 mg, 92% yield).

References:

ARRAY BIOPHARMA INC.;GENENTECH, INC.;AHRENDT, Kateri A.;BUCKMELTER, Alexandre J.;DE MEESE, Jason;GRINA, Jonas;HANSEN, Joshua D.;LAIRD, Ellen R.;LUNGHOFER, Paul;MORENO, David;NEWHOUSE, Brad;REN, Li;SEO, Jeongbeob;TIAN, Hongqi;WENGLOWSKY, Steven Mark;FENG, Bainian;GUNZNER, Janet;MALESKY, Kim;MATHIEU, Simon;RUDOLPH, Joachim;WEN, Zhaoyang;YOUNG, Wendy B. WO2009/111279, 2009, A1 Location in patent:Page/Page column 84