Cesium fluoride → 2-methoxy-N-(6-methoxypyridin-3-yl)-5-(4-methyl-6-(methylthio)-1,3,5-triazin-2-yl)pyrimidin-4-amine

Participants

Reaction Conditions

Reaction Steps

A glass microwave reaction vessel was charged with 5-iodo-2-methoxy-N-(6-methoxypyridin-3-yl)pyrimidin-4-amine (120 mg, 0.335 mmol), 2-methyl-4-(methylthio)-6-(tributylstannyl)-1,3,5-triazine (144 mg, 0.335 mmol), copper(I) iodide (13 mg, 0.067 mmol), cesium fluoride (102 mg, 0.670 mmol), tetrakis(triphenylphosphine)palladium(0) (38.7 mg, 0.034 mmol) and dioxane (2 mL). The reaction mixture was stirred and heated in a Emrys Optimizer microwave reactor (Personal Chemistry, Biotage AB, Inc., Upssala, Sweden) at 140° C. for 30 min. The reaction mixture was diluted with water (10 mL) and extracted with EtOAc (2×30 mL). The organic extract was washed with saturated NaCl (5 mL) and dried over Na2SO4. The solution was filtered and concentrated in vacuo to give the crude material as orange solid. The crude product was purified by silica gel chromatography eluting with 60% EtOAc/hexanes to give 2-methoxy-N-(6-methoxypyridin-3-yl)-5-(4-methyl-6-(methylthio)-1,3,5-triazin-2-yl)pyrimidin-4-amine (86 mg, 0.232 mmol, 69.1% yield). 1H NMR (300 MHz, CDCl3) δ 11.78 (s, 1H); 9.53 (s, 1H); 8.39 (s, 1H); 8.06 (dd, J=8.77, 1.90 Hz, 1H); 6.80 (d, J=8.92 Hz, 1H); 4.01 (s, 3H); 3.96 (s, 3H); 2.63 (s, 6H). m/z (ESI, +ve ion) 372.0 (M+H)+.

Provenance & Evidence