Triphenylphosphine → 1-(3-bromopropyl)-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Participants

Reaction Conditions

Reaction Steps

A suspension of 3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine (10.00 g, 38.31 mmol) in tetrahydrofuran (150 mL) was treated with 3-bromo-1-propanol (15.98 g, 114.93 mmol) and triphenylphosphine (20.1 g, 76.62 mmol). Diethylazodicarboxyate (13.34 g, 76.62 mmol) was slowly added to the reaction mixture. The reaction mixture was stirred at 0° C. for 30 min, after which the ice bath was removed and was stirred for 30 minutes at room temperature. The reaction mixture was partially concentrated and ethyl acetate (200 mL) was added. The precipitate was filtered and the filtrate was concentrated to dryness. The crude compound was purified by flash chromatography on silica gel using 100% ethyl acetate as the eluent. The afforded 7.8 g (53%) of 1-(3-bromopropyl)-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine. 1H NMR (DMSO-d6, 400 MHz) δ 8.230 (s, 1H), 4.419-4.385 (t, 2H), 3.530-3.498 (t, 2H), 2.370-2.304 (q, 2H); LCMS (Thermoquest AQA single-quad MS, Genesis C18 column, 3 μm particle size, 33×4.6 mm; 70% 50 mM ammonium acetate in water to 95% acetonitrile over 6 min, 0.8 to 0.5 mL/min) Rt 2.05 min (100%), MH+ 422.9.

Provenance & Evidence