Methylhydrazine → 4-(azetidin-1-yl)-1-methyl-3-{1-methyl-5-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazol-4-yl}-1H-pyrazolo[3,4-d]pyrimidine

Participants

Reaction Steps

Methylhydrazine (98%, 0.254 mL, 4.73 mmol) was added to a solution of [4-(azetidin-1-yl)-6-chloropyrimidin-5-yl]{1-methyl-5-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazol-4-yl}methanone (C16) (200 mg, 0.473 mmol) in 1,4-dioxane (4 mL), and the reaction mixture was allowed to stir for 18 hours at room temperature. After removal of solvent in vacuo, the residue was chromatographed on silica gel to provide the product as a solid. Yield: 120 mg, 0.290 mmol, 61%. LCMS m/z 415.0 (M+1). 1H NMR (400 MHz, CD3OD) δ 2.25-2.34 (m, 2H), 3.79-4.04 (br m, 4H), 3.94 (s, 3H), 3.98 (s, 3H), 7.80 (s, 1H), 7.85 (d, J=8.2 Hz, 1H), 8.12-8.16 (m, 1H), 8.17 (s, 1H), 8.77-8.79 (m, 1H).

Provenance & Evidence