Nitrogen → HCID 16049103, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-(4-(6-bromo-4-oxo-thieno[3,2-d]pyrimidin-3(4H)-yl)-2-methoxyphenoxy)-2-methyl-2-propanol (50 mg, 0.12 mmol), 2,4-dichlorobenzeneboronic acid (21 mg, 0.18 mmol), Na2CO3 (31 mg, 0.29 mmol), tetrakis(triphenylphosphine)palladium (10 mg, 0.0088 mmol), N2-degassed dioxane (1 mL) and N2-degassed water (0.5 mL) was heated in a 110° C. bath for 30 min. The mixture, upon cooling, was poured into half-saturated NaHCO3 (3 mL). The mixture was extracted with CH2Cl2 (2×5 mL). The combined organic layers were dried (MgSO4) and concentrated in vacuo. The residue was chromatographed (4 g silica, CH2Cl2 to 50% EtOAc-CH2Cl2) to provide 1-(4-(6-(2,4-dichlorophenyl)-4-oxo-thieno[3,2-d]pyrimidin-3(4H)-yl)-2-methoxyphenoxy)-2-methyl-2-propanol as an off-white solid (41 mg, 71%). 1H-NMR (CDCl3) δ 8.09 (s, 1 H), 7.54 (s, 1 H), 7.49 (m, 2 H), 7.29 (dd, J=8, 2 Hz, 1 H), 6.84-6.96 (m, 3 H), 3.81 (s, 5 H), 1.30 (s, 6H); HPLC (Method #7) 4.2 min; LCMS (ES) m/z 491 (M+H).

Provenance & Evidence