2-[4-(4-Morpholin-4-yl-2-(tributylstannanyl)-thieno[3,2-d]pyrimidin-6-ylmethyl)piperazin-1-yl]isobutyramide → HCID 49834392, 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 (72 mg, 0.10 mmol), 4-bromo-5-methyl-1H-pyrrolo[2,3-c]pyridine (22 mg, 0.10 mmol), Pd(PPh3)4 (12 mg, 10 mol %) and copper(I)-thiophene-2-carboxylate (4 mg, 20 mol %) in dioxane (1 mL) was purged with argon gas then heated at 150° C., for 20 min, in a microwave reactor. The reaction mixture was loaded onto an Isolute® SCX-2 cartridge, the cartridge was washed with MeOH then the desired product eluted with 2 M NH3 in MeOH. The resulting residue was purified by column chromatography (Si—PCC, 0-20% MeOH in DCM) to give 153 as a pale yellow solid (24 mg, 43%). LCMS (Method E): RT=4.19 min, [M+H]+ 535.2. 1H NMR (400 MHz, CHCl3-d): δ 9.14 (s, 1 H), 8.73 (s, 1 H), 7.34-7.32 (m, 2 H), 7.11 (d, J=5.3 Hz, 1 H), 6.67-6.65 (m, 1H), 5.30 (d, J=4.7 Hz, 1 H), 4.04 (t, J=4.7 Hz, 4 H), 3.87 (d, J=4.7 Hz, 4 H), 3.85 (s, 2H), 2.76 (s, 3 H), 2.61 (m, 8 H), 1.28-1.22 (m, 6 H)

Provenance & Evidence