Sodium Thiosulfate → HCID 60155988, compound

Participants

Reaction Steps

4-(2-Fluoro-5-(4-(methylthio)benzyl)pyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine (624.5 mg, 1.074 mmol) was dissolved in DCM (11 mL) and the flask was cooled in an ice water bath. Then, mCPBA (557 mg, 3.23 mmol) was added as a solution in DCM (17.5 mL) and the reaction was warmed to room temperature and stirred under nitrogen. After 35 min, the reaction was treated with a mixture of saturated sodium bicarbonate (25 mL) and saturated sodium thiosulfate (6 mL), and stirring was continued at room temperature. After 50 minutes, the layers were separated, and the aqueous phase was extracted with DCM. The organic phase was dried over sodium sulfate, filtered, concentrated, and purified on a silica gel filter (30 mL fritted filter with about 1 inch of silica gel; DCM to 50:1 DCM/MeOH) to give 4-(2-fluoro-5-(4-(methylsulfonyl)benzyl)pyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine (539.6 mg, 75% yield based on 91% purity). 1H NMR (CDCl3, 400 MHz) δ 8.34 (dd, J=8.90 Hz, 2.45 Hz, 1H), 8.16 (d, J=1.76 Hz, 1H), 7.89 (d, J=8.41 Hz, 2H), 7.40 (d, J=8.22 Hz, 2H), 7.21 (d, J=8.61 Hz, 4H), 6.90-6.82 (m, 4H), 4.82 (s, 2H), 4.79 (s, 2H), 4.13 (s, 2H), 3.82 (s, 3H), 3.80 (s, 3H), 3.03 (s, 3H), 2.54 (s, 3H). m/z (ESI, +ve ion) m/z 614 (M+H)+.

Provenance & Evidence