Sodium Carbonate → HCID 118092764, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-methoxy-N-(3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidin-2-amine (0.045 g, 0.13 mmol), ethyl 3-(6-bromopyridin-2-yl)propanoate (0.037 g, 0.15 mmol), PdCl2(dppf)-CH2Cl2 (0.016 g, 0.020 mmol), and Na2CO3 (2.0 M in water, 0.13 mL, 0.26 mmol) in dioxane (0.75 mL) was purged with argon and heated to 110° C. for 12 hours. Upon cooling, NaOH (1.0 M in water, 0.50 mL) and MeOH (0.50 mL) were added to the reaction mixture and irradiated in a microwave reactor for 10 minutes at 110° C. Silica Supported-DMT (0.088 g, 0.13 mmol, 0.57 mmol/g) was added to the reaction mixture and shaken for 5 hours at ambient temperature. The reaction was passed through a syringe filter and the eluent was evaporated under reduced pressure. The residue was suspended in DMSO (1.5 mL) and was purified by reverse phase preparative HPLC (0:100 to 95:5 acetonitrile:water: 0.1% v/v formic acid modifier) to afford methyl 3-(6-(3-((4-methoxypyrimidin-2-yl)amino)-5-methylphenyl)pyridin-2-yl)propanoate. LRMS (ESI) calc'd for C20H21N4O3 [M+H]+: 365. Found: 365. 1H NMR (600 MHz, DMSO-d6) δ 9.54 (s, 1H), 8.33 (s, 1H), 8.18 (d, J=5.6, 1H), 7.73 (t, J=7.7, 1H), 7.64 (d, J=7.8, 1H), 7.61 (s, 1H), 7.44 (s, 1H), 7.19 (d, J=7.6, 1H), 6.25 (d, J=5.6, 1H), 3.93 (s, 3H), 2.99 (t, J=7.4, 2H), 2.71 (t, J=7.4, 2H), 2.33 (s, 3H).

Provenance & Evidence