Sodium Thiosulfate → 4-(2-fluoro-5-(1-(4-(methylsulfonyl)phenyl)ethyl)pyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine

Participants

Reaction Steps

4-(2-Fluoro-5-(1-(4-(methylthio)phenyl)ethyl)pyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine (1.797 g, 3.016 mmol) was dissolved in DCM (30 mL) and the reaction flask was cooled in an ice water bath under nitrogen. Then, 3-chlorobenzoperoxoic acid (1.668 g, 9.666 mmol) was added as a solution in DCM (52 mL), and the reaction was warmed to room temperature and stirred. After 30 min, the reaction was cooled in an ice water bath and treated with a mixture of saturated sodium bicarbonate (50 mL) and saturated sodium thiosulfate (15 mL). The biphasic mixture was warmed to room temperature and stirred. After 1 h, the layers were separated, and the aqueous phase was extracted with DCM. The organic phases were combined, dried over sodium sulfate, filtered, concentrated, and purified on a silica gel filter (150 mL fritted filter with about 2 inches of silica gel; DCM to 100:1 DCM/MeOH to 50:1 DCM/MeOH). The fractions with product were collected, concentrated, and dried under high vacuum to give 4-(2-fluoro-5-(1-(4-(methylsulfonyl)phenyl)ethyl)pyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine (1.517 g). 1H NMR (CDCl3, 400 MHz) δ 8.34 (dd, J=8.90 Hz, 2.45 Hz, 1H), 8.17 (s, 1H), 7.88 (d, J=8.41 Hz, 2H), 7.42 (d, J=8.22 Hz, 2H), 7.21 (d, J=8.02 Hz, 4H), 6.86 (t, J=8.90 Hz, 4H), 4.82 (s, 2H), 4.78 (s, 2H), 4.34 (q, J=7.69 Hz, 1H), 3.82 (s, 3H), 3.81 (s, 3H), 3.02 (s, 3H), 2.54 (s, 3H), 1.74 (d, J=7.24 Hz, 3H). m/z (ESI, pos. ion) 628 (M+H)+.

Provenance & Evidence