Ammonia → 5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-N4-(6-methoxypyridin-3-yl)-N2,N2-dimethylpyrimidine-2,4-diamine

Participants

Reaction Conditions

Reaction Steps

A glass microwave reaction vessel was charged with N4-(6-methoxypyridin-3-yl)-N2,N2-dimethyl-5-(4-methyl-6-(methylthio)-1,3,5-triazin-2-yl)pyrimidine-2,4-diamine (16 mg, 0.042 mmol), ammonia (0.5 mL, 23.11 mmol) (30% in water) and dioxane (1 mL). The reaction mixture was stirred and heated in an oil bath at 100° C. for 16 h. The solvent was removed in vacuo and the residue was purified by silica gel chromatography eluting with 5% MeOH/EtOAc to give 5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-N4-(6-methoxypyridin-3-yl)-N2,N2-dimethylpyrimidine-2,4-diamine (11 mg, 0.031 mmol, 74.8% yield). 1H NMR (300 MHz, CDCl3) δ 11.94 (s, 1H); 9.29 (s, 1H); 8.42 (s, 1H); 8.07 (dd, J=8.92, 2.34 Hz, 1H); 6.76 (d, J=8.77 Hz, 1H); 5.29 (s, 2H); 3.95 (s, 3H); 3.23 (s, 6H); 2.48 (s, 3H). m/z (ESI, +ve ion) 354.0 (M+H)+.

Provenance & Evidence