反应详情

To a slurry of 4-(5-(ethylsulfinyl)-2-(5-fluoro-6-methoxypyridin-3-ylamino)pyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine (0.090 g, 0.140 mmol) in 2 mL MeOH, 2 mL dioxane, and 1 mL water was added potassium peroxymonosulfate sulfate (0.172 g, 0.280 mmol). The bright yellow slurry was stirred rapidly overnight. The reaction was partitioned between satd NaHCO3 and DCM. The aqueous layer was extracted with DCM 3 times, and the combined organics were dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The material was treated with DCM and purified by silica gel chromatography (25 g column) using 20 to 100% EtOAc/hexane. The product-containing fractions were concentrated to afford 4-(5-(ethylsulfonyl)-2-(5-fluoro-6-methoxypyridin-3-ylamino)pyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine (0.066 g, 0.100 mmol, 71.6% yield) as a yellow solid. m/z (ESI, +ve ion) 660 (M+H)+. 1H NMR (400 MHz, CDCl3) δ 11.91 (s, 1H), 8.80 (d, J=2.7 Hz, 1H), 8.43 (d, J=2.7 Hz, 1H), 8.15-8.33 (m, 2H), 7.14-7.25 (m, 4H), 6.80-6.93 (m, 4H), 4.87 (s, 2H), 4.83 (s, 2H), 4.02 (s, 3H), 3.82 (s, 3H), 3.79 (s, 3H), 3.07-3.22 (m, 1H), 2.82-2.94 (m, 1H), 2.62 (s, 3H), 1.28 (t, J=7.4 Hz, 3H).

1. customThe reaction was partitioned between satd NaHCO3 and DCM
2. extractionThe aqueous layer was extracted with DCM 3 times
3. dry with materialthe combined organics were dried over anhydrous sodium sulfate
4. filtrationfiltered
5. concentrationconcentrated in vacuo
6. additionThe material was treated with DCM
7. custompurified by silica gel chromatography (25 g column)
8. concentrationThe product-containing fractions were concentrated