Methanesulfonic Acid → HCID 58456197, compound

Participants

Reaction Conditions

Reaction Steps

The product of Step 1 (107 mg, 0.528 mmol) and 3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (123 mg, 0.528 mmol) were dissolved in Dioxane (4 ml), and methanesulfonic acid (0.036 ml, 0.554 mmol) was added. The mixture was heated to 100° C. for 18 h. The mixture was allowed to cool to room temperature, quenched with saturated aqueous sodium bicarbonate and extracted with EtOAc (2×). The combined organic layers were dried over Na2SO4 and concentrated in vacuo to afford 4-(3-methoxypropoxy)-N-[3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]pyrimidin-2-amine (165 mg, 78%) as a brown solid. MS ESI: [M+H]+ m/z 400. 1H NMR (500 MHz, CDCl3) δ 8.09 (d, J=5.8, 1H), 7.82 (s, 1H), 7.59 (s, 1H), 7.32 (s, 1H), 6.17 (d, J=4.4, 1H), 4.48 (t, J=5.8, 2H), 3.53 (t, J=5.5, 2H), 3.34 (s, 3H), 2.37 (s, 3H), 2.05 (dd, J=3.3, 9.4, 2H), 1.34 (s, 12H).

Provenance & Evidence