4-Chlorothieno[3,2-d]pyrimidine → [1-(4-Chlorobenzyl)-2-oxo-2-(4-thieno[3,2-d]pyrimidin-4-yl-piperazin-1-yl)-ethyl]-carbamic acid tert-butyl ester

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The solution of [1-(4-chlorobenzyl)-2-oxo-2-piperazin-1-yl-ethyl]-carbamic acid tert-butyl ester (60 mg, 0.163 mmol) and 4-Chlorothieno[3,2-d]pyrimidine 950 mg, 0.293 mmol) in Toluene (5 mL)/TEA (1 mL) was refluxed for 12 hours. After the solvent was removed, the residue was subject to chromatography on silica gel to afford [1-(4-chlorobenzyl)-2-oxo-2-(4-thieno[3,2-d]pyrimidin-4-yl-piperazin-1-yl)-ethyl]-carbamic acid tert-butyl ester (71 mg, 86.7%). 1H NMR (CDCl3, 400 Hz) δ 8.60 (s, 1H), 7.76 (d, J=5.2 Hz, 1H), 7.45 (d, J=5.2 Hz, 1H), 7.26 (d, J=8.4 Hz, 1H), 7.15 (d, J=8.4 Hz, 1H), 5.39 (d, J=8.8 Hz, 1H), 4.88-4.82 (m, 1H), 3.94-3.76 (m, 4H), 3.69-3.58 (m, 3H), 3.25-3.22 (m, 1H), 2.98 (d, J=7.2 Hz, 2H), 1.43 (s, 9H). MS (ESI+) [M+H]+ 503.

Provenance & Evidence