Acetic Acid → HCID 58095180, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 7-[5-(1-allyl-1H-imidazol-2-yl)-4-(2,4-dichlorophenyl)-2-thienyl]-N-(tert-butyl)[1,3]thiazolo[5,4-d]pyrimidin-2-amine (100 mg, 0.185 mmol) and acetic acid (2 mL, 40 mmol) in DCM (6 mL) was degassed with vacuum and then the atmosphere was replaced with nitrogen. To the mixture, tetrakis(triphenylphosphine)palladium(0) (10.7 mg, 0.00923 mmol) and phenylsilane (0.136 mL, 1.11 mmol) were added. The resulting mixture was stirred at 40° C. for 30 min. The solution was allowed to cool to rt, followed by adding water and DCM. After being stirred for 10 min, the organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. Column chromatography was performed to yield the title compound (46.0 mg, 50%) as a pale yellow solid. LCMS: (AA) ES+ 501, 503. 1H NMR (400 MHz, d6-DMSO) δ: 11.84 (bs, 1H), 8.69 (bs, 1H), 8.63 (s, 1H), 8.43 (s, 1H), 7.73 (d, J=2.0 Hz, 1H), 7.46-7.43 (m, 1H), 7.34 (d, J=8.3 Hz, 1H), 7.14 (bs, 1H), 6.98 (bs, 1H), 1.47 (s, 9H).

Provenance & Evidence