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

Participants

Reaction Conditions

Reaction Steps

A solution of 4-(5-(2-aminopropan-2-yl)-2-(6-methoxypyridin-3-ylamino)pyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine (0.025 g, 0.041 mmol) in TFA (1 mL) was treated with triflic acid (0.029 mL, 0.330 mmol), sealed, and heated at 80° C. for 2 h. The reaction was 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 (3×) and the combined organic extracts were dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. This material was dissolved in DMSO and purified by prep HPLC (5-50% MeCN/H2O with 0.1% TFA). Product-containing fractions were concentrated in vacuo to give 4-(5-(2-aminopropan-2-yl)-2-(6-methoxypyridin-3-ylamino)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine 2,2,2-trifluoroacetate (9 mg, 0.019 mmol, 45.5% yield) as an orange solid. m/z (ESI, +ve ion) 367 (M+H)+. 1H NMR (400 MHz, d6-DMSO) δ 11.76 (s, 1H); 8.93 (d, J=2.7 Hz, 1H); 8.54 (d, J=2.5 Hz, 1H); 8.50 (d, J=2.7 Hz, 1H); 8.37 (br. s., 3H); 8.13 (dd, J=8.8, 2.7 Hz, 1H); 7.90 (br. s., 1H); 7.80 (br. s., 1H); 6.84 (d, J=9.0 Hz, 1H); 3.85 (s, 3H); 2.45 (s, 3H); 1.68 (s, 6H).

Provenance & Evidence