1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → 9-(4,4-Dimethylcyclohexyl)-8-methoxy-9H-pyrido[4',3':4,5]pyrrolo[2,3-d]pyrimidin-2-amine

Participants

Reaction Steps

To a 30 mL microwave reaction vessel were placed compound 332 (0.55 g, 1.5 mmol), tris(dibenzylideneacetone)dipalladium (0) (0.14 g, 0.15 mmol), 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (0.22 g, 0.38 mmol), and sodium tert-butoxide (0.37 g, 3.8 mmol) followed by 1,4-dioxane (15 mL). The vessel was purged with N2 for 5 min, then capped and subjected to microwave condition (3 h at 140° C.). After the volatiles were removed, the crude mixture was taken up in 4% methanol/DCM and subjected to combi-flash column chromatography (1% to 7% methanol in DCM) to give crude compound 333 as an off-white solid (0.65 g). 1H NMR (500 MHz, DMSO-d6) δ ppm 9.01 (1 H, s), 7.92 (1 H, d, J=5.1 Hz), 7.59 (1 H, d, J=4.9 Hz), 6.86 (2 H, br. s.), 4.98-5.14 (1 H, m), 4.06 (3 H, s), 1.53 (4 H, br. s.), 1.31-1.44 (2 H, m), 1.16 (3 H, s), 1.00 (3 H, s). LCMS-ESI (POS), M/Z, M+1: Found 326.1.

Provenance & Evidence