tert-Butylsulfinamide, (S)-(-)- → tert-butyl 4-[5-[(Z)-N-[(S)-tert-butylsulfinyl]-C-(4-fluorophenyl)carbonimidoyl]pyrimidin-2-yl]piperazine-1-carboxylate

Participants

Reaction Steps

To a solution of tert-butyl 4-(5-(4-fluorobenzoyl)pyrimidin-2-yl)piperazine-1-carboxylate (4.0 g, 10.4 mmol), (S)-2-methylpropane-2-sulfinamide (2.5 g, 20.7 mmol) in THF (60 mL) was added titanium ethoxide (20 mL) at room temperature. The resultant solution was heated at 70° C. overnight. After that, the reaction was cooled to room temperature, diluted with ethyl acetate (200 mL) and saturated aqueous sodium bicarbonate (500 mL). The mixture was filtered through Celite. The filtrate was separated. Aqueous layer was extracted with ethyl acetate (200 mL×3). Then organic layers were combined, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel column (petroleum ether:ethyl acetate 2:1) to afford the title compound (3.3 g, yield 66%) as a yellow solid. MS (ES+) requires: 489, found 490 [M+H]+; purity: 95% (UV at 254 nm).

Provenance & Evidence