Ammonia → 4-(4-(6-Methoxypyridin-3-ylamino)-2-(pyridin-4-yl)pyrimidin-5-yl)-6-methyl-1,3,5-triazin-2-amine

Participants

Reaction Conditions

Reaction Steps

A glass microwave reaction vessel was charged with N-(6-methoxypyridin-3-yl)-5-(4-methyl-6-(methylthio)-1,3,5-triazin-2-yl)-2-(pyridin-4-yl)pyrimidin-4-amine (8 mg, 0.019 mmol), ammonia (0.5 mL, 23.11 mmol) (30% in water) and dioxane (1 mL). The reaction mixture was stirred and heated in a Emrys Optimizer microwave reactor (Personal Chemistry, Biotage AB, Inc., Upssala, Sweden) at 100° C. for 18 h. The solvent was removed in vacuo and the residue was purified by silica gel chromatography eluting with 10% MeOH/EtOAc to give 4-(4-(6-methoxypyridin-3-ylamino)-2-(pyridin-4-yl)pyrimidin-5-yl)-6-methyl-1,3,5-triazin-2-amine (4 mg, 10.33 μmol, 54.0% yield). 1H NMR (300 MHz, d6-DMSO) δ 11.96 (s, 1H); 8.77 (d, J=5.12 Hz, 1H); 8.59 (s, 1H); 8.21 (dd, J=9.06, 2.34 Hz, 1H); 8.15 (d, J=5.12 Hz, 1H); 7.99 (s, 1H); 7.82 (s, 1H); 6.96 (d, J=8.77 Hz, 1H); 3.90 (s, 2H); 2.45 (s, 3H). m/z (ESI, +ve ion) 388.1 (M+H)+.

Provenance & Evidence