3-methyl-1-(oxan-4-yl)-1H-pyrazol-5-amine → Ethyl 6-cyclopropyl-3-methyl-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-methyl-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazol-5-amine (380 mg, 2.097 mmol), ethyl (3Z)-4-cyclopropyl-4-hydroxy-2-oxo-3-butenoate (386 mg, 2.097 mmol) and acetic acid (50 mL) were heated at 117° C. for 2 hours. The solvent was removed in vacuo, and the crude residue was purified via silica gel chromatography (eluent: 0 to 25% EtOAc:Hex). The desired product was collected as a solid, 300 mg (43%). LCMS E-S (M+H)=330.3 1H NMR (400 MHz, DMSO-d6) δ ppm 1.00-1.12 (m, 4 H), 1.37 (t, J=7.20 Hz, 3 H), 1.82 (dd, J=12.51, 2.40 Hz, 2 H), 2.16 (qd, J=12.21, 4.55 Hz, 2 H), 2.29-2.42 (m, 1 H), 2.54 (s, 3 H), 3.47-3.60 (m, 2 H), 3.99 (dd, J=11.37, 3.79 Hz, 2 H), 4.42 (q, J=7.24 Hz, 2 H), 4.92 (tt, J=11.59, 4.20 Hz, 1 H), 7.46 (s, 1 H).

Provenance & Evidence