1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 67540094, compound

Participants

Reaction Steps

To a solution of 4-(4-Benzyl-piperazin-1-yl)-6-methylthieno[3,2-d]pyrimidine (65 mg, 0.20 mmol) in MeOH (10 mL) was added Pd/C (10%, 20 mg) and two drop of TFA. The mixture was stirred under H2 balloon for 4 hours. The catalyst was filtered off and the filtrate was concentrated. The residue was dissolved in DCM (6 mL) and TEA (2 mL), then Boc-D-Phe(4-Cl)—OH (59 mg, 0.20 mmol) was added, followed by HOBT (50 mg, 0.37 mmol) and EDCI (74 mg, 0.39 mmol). The mixture was stirred at room temperature for 12 hours. The solvent was removed and the residue was subject to chromatography on silica gel to give the product {1-(4-chlorobenzyl)-2-[4-(6-methylthieno[3,2-d]pyrimidin-4-yl)-piperazin-1-yl]-2-oxo-ethyl}-carbamic acid tert-butyl ester (60 mg, 59%). 1H NMR (CDCl3, 400 Hz) δ 8.54 (s, 1H), 7.28-7.26 (d, J=7.2 Hz, 2H), 7.17-7.15 (d, J=8.4 Hz, 2H), 7.08 (s, 1H), 5.37-5.35 9d, J=8.8 Hz, 1H), 4.86-4.84 (m, 1H), 3.87-3.57 (m, 7H), 3.24-3.22 (m, 1H), 3.00-2.98 (d, J=7.2 Hz, 2H), 2.63 (s, 3H), 1.43 (s, 9H). MS (ESI+) [M+H]+ 516.

Provenance & Evidence