Sodium Carbonate → 5-[4-Morpholino-7-(trifluoromethyl)-6,7-dihydro-[1,4]dioxino[2,3-d]pyrimidin-2-yl]pyrimidin-2-amine

Participants

Reaction Conditions

Reaction Steps

A microwave vial was charged with 2-chloro-4-morpholin-4-yl-7-trifluoromethyl-6,7-dihydro-[1,4]dioxino[2,3-d]pyrimidine (105 mg, 0.32 mmol), 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyrimidin-2-ylamine (143 mg, 0.64 mmol), Pd(PPh3)2Cl2 (23 mg, 0.03 mmol) and sodium carbonate (1.06 mL, 1.06 mmol, 1M aqueous solution) in acetonitrile (1.6 mL) before the vessel was evacuated and back filled with argon (×3). The mixture was heated at 120° C. for 30 minutes using microwaves. The reaction mixture was diluted with H2O/DCM/methanol then absorbed onto diatomaceous earth before being purified by column chromatography (SiO2, gradient 0-4% methanol in DCM then SiO2 then gradient 0-90% ethyl acetate in cyclohexane) followed by trituration in diethyl ether to give 105 as a white solid (60 mg, 49%). LCMS: RT=3.52 min, [M+H]+=385. 1H NMR (400 MHz, DMSO): δ 8.92 (2H, s), 7.08 (2H, s), 5.51-5.41 (1H, m), 4.53-4.41 (2H, m), 3.78-3.65 (8H, m)

Provenance & Evidence