Triacetoxyperiodinane → HCID 86665100, compound

Participants

Reaction Steps

A flask was charged with (1-(2-chlorofuro[3,2-d]pyrimidin-4-yl)piperidin-4-yl)methanol (11.2 g, 41.8 mmol, prepared using A from 2,4-dichlorofuro[3,2-d]pyrimidine [Arkpharm], piperidin-4-ylmethanol), DCM (200 mL) and Dess-Martin periodinane (18.6 g, 43.9 mmol). The mixture was stirred at rt for about 3 h. The mixture was diluted with DCM (100 mL) and washed with an aqueous solution of 1 N Na2CO3 (200 mL). The aqueous layer was extracted with DCM (2×100 mL). The combined extracts were washed with brine, dried over Na2CO3, filtered, and evaporated under vacuum. The residue was purified by column chromatography eluting with 20-80% EtOAc/heptane (120 g silica gel) to provide 1-(2-chlorofuro[3,2-d]pyrimidin-4-yl)piperidine-4-carbaldehyde (10 g, 90%): LC/MS (Table 2, Method u) Rt=1.22 min.; MS m/z: 266 (M+H)+.

Provenance & Evidence