Triethylamine → 4-Amino-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-N-(2,2,2-trifluoroethyl)pyrimidine-5-carboxamide

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Reaction Steps

300 mg (0.82 mmol) of 4-amino-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]pyrimidine-5-carboxylic acid (example 102A), 0.230 ml (1.65 mmol) of triethylamine and 139 mg (0.91 mmol) of 1-hydroxyl-1H-benzotriazole were dissolved in 2.2 ml of DMF, and 174 mg (0.91 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride were added. While cooling with ice, 70 μl (90 mg, 0.91 mmol) of 2,2,2-trifluoroethylamine were added, and the mixture was reacted at room temperature overnight. The mixture was brought into solution with 4 ml of acetonitrile/water and purified by means of preparative HPLC [column: Reprosil C18, 10 μm, 250*40 mm; eluent: acetonitrile/0.05% formic acid; gradient: 15% acetonitrile→95% acetonitrile]. Thus, 110 mg (28% of theory) of the target compound were obtained.

Provenance & Evidence