Triphenylphosphine → HCID 68459531, compound

Participants

Reaction Steps

A suspension of 3-Iodo-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine, prepared as described in A. F. Burchat et al. Bioorg Med. Chem. Lett. 2002, 12, 1687-1690, (0.392 g, 1.5 mmol), 3-(pyridine-3-yl)propan-1-ol (0.388 ml, 3 mmol), and triphenylphosphine (0.983 g, 3.75 mmol) in THF (10 ml) under inert atmosphere was cooled in an ice bath and diisopropyl azodicarboxylate (0.581 ml, 3 mmol) was added dropwise and the reaction was then stirred for 72 hrs at ambient temperature. The reaction was concentrated and the residue was acidified with 1M HCl and washed with EtOAc. The aqueous layer was basified with solid Na2CO3 and extracted with EtOAc. The EtOAc was dried over Na2SO4, filtered and concentrated. The residue was purified on silica gel using an ISCO Companion chromatography system eluted with 0-20% MeOH/CH2Cl2 to give the title compound as an off-white solid (310 mg, 54%). MS (ESI(+)) m/e 381 (M+H)+, (ESI(−)) m/e 379 (M−H)−; 1H NMR (300 MHz, DMSO-d6) 8.39 (m, 2H), 8.20 (s, 1H), 7.61 (dd, 1H), 7.28 (m, 1H), 4.19 (t, 2H), 2.60 (m, 2H), 2.17 (m, 2H).

Provenance & Evidence