Triethylamine → (R)-Tert-butyl 3-(5-(benzo[d]thiazol-2-yl)-6-methoxy-2-morpholinopyrimidin-4-ylamino)piperidine-1-carboxylate

Participants

Reaction Steps

2-Tributylstannylbenzothiazole (221 mg, 0.520 mmol), Compound 21 (150 mg, 0.289 mmol), Tetrakis(triphenylphosphine)palladium (67 mg, 0.0578 mmol), and CuI (11 mg, 0.0578 mmol) were combined. Dioxane (4 mL) was added followed by Et3N (161 μL, 1.16 mmol) and the mixture was degassed and heated to reflux for 2 h. The solution was cooled to room temperature and an aqueous 10% KF solution was added and the mixture was stirred for 30 min. The mixture was diluted with EtOAc and washed with water, brine, dried (MgSO4), filtered and evaporated to dryness. The residue was purified by column chromatography on silica gel, eluting with EtOAc/hexane to give the title compound as a yellow solid. 1H NMR (CDCl3) δ 10.74 (br s, 1H), 7.86-7.82 (m, 2H), 7.41 (t, J=7.2 Hz, 1H), 7.27 (t, J=7.2 Hz, 1H), 4.25 (br s, 1H), 4.09 (s, 3H), 3.87 (br s, 4H), 3.78-3.76 (m, 4H), 3.52 (br s, 4H), 2.03 (br s, 1H), 1.90 (br s, 1H), 1.76-1.73 (m, 1H), 1.66-1.64 (m, 1H), 1.33 (s, 9H); LCMS 3.28 min, 527 (M+H).

Provenance & Evidence