Sodium Hydroxide → 4-(5-(Ethylsulfonyl)-2-(5-fluoro-6-methoxypyridin-3-ylamino)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine

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Reaction Conditions

Reaction Steps

A solution of 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) in trifluoromethanesulfonic acid (0.089 mL, 1.000 mmol) and 1.5 mL TFA was sealed and heated to 70° C. for 30 min, cooled, and treated with ice and 10N NaOH until basic. The reaction was partitioned between water and DCM. The aqueous layer was extracted with DCM 5 times, and the combined organics were dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The resulting yellow solid was suspended in 1 mL EtOAc, filtered, rinsing 2× diethyl ether, and dried in vacuo to give 4-(5-(ethylsulfonyl)-2-(5-fluoro-6-methoxypyridin-3-ylamino)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine (0.029 g, 0.069 mmol, 69% yield) as a yellow solid. m/z (ESI, +ve ion) 420 (M+H)+. 1H NMR (400 MHz, d6-DMSO) δ 11.87 (s, 1H), 8.73 (d, J=2.7 Hz, 1H), 8.52 (d, J=2.7 Hz, 1H), 8.41 (d, J=2.5 Hz, 1H), 8.33 (d, J=2.7 Hz, 1H), 7.98 (br. s., 1H), 7.83 (br. s., 1H), 3.95 (s, 3H), 3.06-3.21 (m, 1H), 2.73-2.89 (m, 1H), 2.44 (s, 3H), 1.09 (t, J=7.3 Hz, 3H).

Provenance & Evidence