1-tert-Butyl-3-methyl-1H-pyrazol-5-amine → ethyl 6-cyclopropyl-1-(1,1-dimethylethyl)-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylate

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The title compound was prepared in the same manner as described for intermediate 33 using ethyl 4-cyclopropyl-2,4-dioxobutanoate (481 mg, 2.61 mmol), 1-(1,1-dimethylethyl)-3-methyl-1H-pyrazol-5-amine (400 mg, 2.61 mmol), and toluene (20 mL), wherein the reaction time was 3 h. The crude product was purified via silica gel chromatography (eluent: 0 to 10% EtOAc:Hex). The final product was collected as 0.24 g (30%). LCMS E-S (M+H)=302.5. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.02-1.23 (m, 4H) 1.47 (t, J=7.20 Hz, 3H) 1.79 (s, 9H) 2.19 (s, 1H) 2.66 (s, 3H) 4.49 (q, J=7.07 Hz, 2H) 7.44 (s, 1H).

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