Methylhydrazine → 4-(azetidin-1-yl)-3-(5-bromo-1-methyl-1H-pyrazol-4-yl)-1-methyl-1H-pyrazolo[3,4-d]pyrimidine

Participants

Reaction Conditions

Reaction Steps

A mixture of methylhydrazine (98%, 1.57 mL, 29.2 mmol) and [4-(azetidin-1-yl)-6-chloropyrimidin-5-yl](5-bromo-1-methyl-1H-pyrazol-4-yl)methanone (C27) (1.04 g, 2.92 mmol) in pyridine (15 mL) was heated to 85° C. for 16 hours. Volatiles were removed in vacuo and the residue was purified using silica gel chromatography (Gradient: 0.5% to 5% methanol in ethyl acetate) to provide the product as a solid. Yield: 960 mg, 2.76 mmol, 94%. LCMS m/z 348.3, 350.2 (M+1). 1H NMR (400 MHz, CDCl3) δ 2.25-2.34 (m, 2H), 3.84-4.04 (br m, 4H), 3.97 (s, 3H), 4.05 (s, 3H), 7.67 (s, 1H), 8.39 (s, 1H).

Provenance & Evidence