Triphenylphosphine → 3-(6-chloro-1-(1,3-dimethoxypropan-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-8-oxa-3-azabicyclo[3.2.1]octane

Participants

Reaction Steps

Diisopropyl azodicarboxylate (1.1 mL, 5.4 mmol) was added in drops to a suspension of 3-(6-chloro-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-8-oxa-3-azabicyclo[3.2.1]octane (1.1 g, 4.1 mmol), 1,3-dimethoxypropan-2-ol (0.65 g, 5.4 mmol), and triphenylphosphine (1.4 g, 5.4 mmol) in tetrahydrofuran (33 mL). When this Mitsunobu reaction was deemed to be complete by LC/MS analysis, the mixture was adsorbed onto flash silica gel and purified by automated flash chromatography (methanol/chloroform) to provide 3-(6-chloro-1-(1,3-dimethoxypropan-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-8-oxa-3-azabicyclo[3.2.1]octane as an amber glass (1.9 g, >100%) contaminated with triphenylphosphine oxide. MS (ES+): 368.2, 370.2 (M+H)+

Provenance & Evidence