2-[4-(4-Morpholin-4-yl-2-(tributylstannanyl)-thieno[3,2-d]pyrimidin-6-ylmethyl)piperazin-1-yl]isobutyramide → HCID 59605699, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-[4-(4-morpholin-4-yl-2-(tributylstannanyl)thieno[3,2-d]pyrimidin-6-ylmethyl)-piperazin-1-yl]isobutyramide (100 mg, 0.14 mmol), 4-bromo-6-methyl-1H-pyrrolo[3,2-c]pyridine (20 mg, 0.09 mmol), tetrakis(triphenylphosphine)palladium (17 mg, 10 mol %) and copper(I)-thiophene-2-carboxylate (6 mg, 20 mol %) in dioxane (1.5 mL) was purged with argon gas then heated at 150° C., for 20 min, in a microwave reactor. The cooled reaction mixture was loaded onto an Isolute® SCX-2 cartridge, washed with MeOH/DCM then eluted with 2 M NH3 in MeOH/DCM. The resulting residue was purified by column chromatography (Si—PPC, 2 M NH3 in MeOH:DCM, gradient 0:100 to 10:90) followed by reverse phase HPLC (Phenomenex Gemini 5 μm C18, 20 mM triethylamine in water on a gradient of acetonitrile 90:10 to 02:98) to give 170 as an off-white solid (11 mg, 22%). LCMS RT 5.14 min, [M+H]+ 535. 1H NMR (CDCl3, 400 MHz) δ 7.41 (s, 1 H), 7.29-7.25 (m, 2 H), 7.14 (s, 1 H), 7.09 (d, J=5.3 Hz, 1 H), 5.36 (d, J=5.3 Hz, 1 H), 4.07 (t, J=4.6 Hz, 4 H), 3.88 (t, J=4.6 Hz, 4 H), 3.83 (s, 2 H), 2.70 (s, 3 H), 2.58 (m, 8 H), 1.23 (s, 6 H)

Provenance & Evidence