Sodium Carbonate → {1-(4-Chlorobenzyl)-2-oxo-2-[4-(6-thiophen-3-yl-thieno[3,2-d]pyrimidin-4-yl)-piperazin-1-yl]-ethyl}-carbamic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of {1-(4-chlorobenzyl)-2-[4-(6-iodothieno[3,2-d]pyrimidin-4-yl)-piperazin-1-yl]-2-oxo-ethyl}-carbamic acid tert-butyl ester (50 mg, 0.080 mmol) in DMF (3 mL) were added 2M Na2CO3 (0.1 mL) and 3-thiophenyl boronic acid (15 mg, 0.117 mmol). The mixture was bubbled N2 for 20 minutes and then Pd(PPh3)4 (10 mg, 0.012 mmol) was added. The mixture was heated to 90° C. for 12 hours. The solvent was removed under vacuum and the residue was subject to chromatography on silica gel to afford the product {1-(4-chlorobenzyl)-2-oxo-2-[4-(6-thiophen-3-yl-thieno[3,2-d]pyrimidin-4-yl)-piperazin-1-yl]-ethyl}-carbamic acid tert-butyl ester (16 mg, 34.4%). 1H NMR (CDCl3, 400 Hz) δ 8.57 (s, 1H), 7.70-7.42 (m, 4H), 7.27 (d, J=8.4, 2H), 7.16 (d, J=8.4 Hz, 2H), 5.36 (d, J=8.8 Hz, 1H), 4.87-4.84 (m, 1H), 3.91-3.59 (m, 7H), 3.27-3.24 (d, J=11.2 Hz, 1H), 3.00-2.99 (d, J=7.2 Hz, 2H), 1.43 (s, 9H). MS (ESI+) [M+H]+ 584.

Provenance & Evidence