Sodium Thiosulfate → HCID 66599927, compound

Participants

Reaction Steps

(6-(6-methoxypyridin-3-ylamino)-5-(2-methyl-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl)pyridin-3-yl)(4-(methylthio)phenyl)methanol (241 mg, 0.423 mmol) was dissolved in DCM (4.0 mL) and the reaction flask was cooled in an ice water bath under nitrogen. Then, mCPBA (180.5 mg, 1.046 mmol) was added as a solution in DCM (5 mL) via syringe, and the reaction was warmed to room temperature and stirred. After 45 min, more mCPBA (58 mg, 0.34 mmol) was added, and stirring was continued. After 25 min, more mCPBA (27.3 mg, 0.158 mmol) was added, and stirring was continued. After 15 minutes, the reaction was treated with a solution made of 10 mL saturated sodium bicarbonate and 2 mL saturated sodium thiosulfate. The mixture was stirred at room temperature for 30 min. Then, the layers were separated and the aqueous phase was extracted with DCM and then with 10:1 DCM/MeOH. The organic extracts were combined, washed with brine, concentrated, and dried under high vacuum in a water bath (about 40° C.) to give (6-(6-methoxypyridin-3-ylamino)-5-(2-methyl-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl)pyridin-3-yl)(4-(methylsulfonyl)phenyl)methanol, which was taken on directly to the next step. 1H NMR (CDCl3, 400 MHz) δ 12.54 (s, 1H), 9.75 (s, 1H), 8.40 (s, 1H), 8.27-8.21 (m, 2H), 8.17 (d, J=8.22 Hz, 1H), 7.95-7.89 (m, 2H), 7.74-7.68 (m, 2H), 6.78 (d, J=10.17 Hz, 1H), 6.01 (s, 1H), 5.85 (d, J=11.93 Hz, 1H), 4.21 (d, J=13.11 Hz, 1H), 3.95 (s, 3H), 3.87-3.77 (m, 1H), 3.03 (s, 3H), 2.97-2.89 (m, 1H), 2.89 (s, 3H), 2.19-1.95 (m, 3H), 1.93-1.65 (m, 3H). m/z (ESI, +ve ion) 602 (M+H)+.

Provenance & Evidence