2-[4-(4-Morpholin-4-yl-2-(tributylstannanyl)-thieno[3,2-d]pyrimidin-6-ylmethyl)piperazin-1-yl]isobutyramide → 2-methyl-2-(4-((4-morpholino-2-(1H-pyrrolo[2,3-c]pyridin-3-yl)thieno[3,2-d]pyrimidin-6-yl)methyl)piperazin-1-yl)propanamide

Participants

Reaction Conditions

Reaction Steps

To a mixture of 2-[4-(4-morpholin-4-yl-2-tributylstannanyl-thieno[3,2-d]pyrimidin-6-ylmethyl)-piperazin-1-yl]-isobutyramide (275 mg, 0.396 mmol), 3-bromo-pyrrolo[2,3-c]pyridine-1-carboxylic acid tert-butyl ester (177 mg, 0.596 mmol), copper(I) thiophene-2-carboxylate (76 mg, 0.40 mmol), and Pd(PPh3)4 (46 mg, 0.040 mmol) was added 1,4-dioxane (2 mL). The reaction vessel was evacuated and back filled with argon under sonication. The reaction mixture was heated in the microwave at 140° C. for 20 minutes. The reaction mixture volume was doubled with a solution of 10% MeOH in DCM. The mixture was filtered through a plug of solka floc and the filtrate was concentrated. The green residue was triturated with hexane and dried in vacuo. The light green solid was purified by flash chromatography (silica, 0-10% of a 9:1 MeOH/NH4OH solution in DCM) to give 137 (20.6 mg, 10%) as an off-white solid. LCMS: M+H+=521. 1H-NMR (300 MHz, DMSO-d6): δ 12.0 (s, 1H), 8.79 (s, 1), 8.39 (d, 1H), 8.37 (d, 1H), 8.23 (d, 1H), 7.35 (s, 1H), 7.07 (d, 1H), 6.95 (d, 1H), 3.97 (m, 4H), 3.83 (m, 6), 2.55 (m, 4H), 2.46 (m, 4H), 1.08 (s, 6H)

Provenance & Evidence