Diisopropylethylamine → HCID 67537431, compound

Participants

Reaction Steps

DIEA (0.74 mL) and HBTU (1.3 g) was added to the solution of (2R)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid (0.092 g) in THF (5 mL) at 0° C. The mixture was stirred at room temperature for 20 minutes, and then 4-piperazin-1-yl-pyrido[2,3-d]pyrimidine (0.31 g) was added. The reaction was stirred at room temperature for 1 hour. 20 mL of EtOAc was added and the organic layer was separated. The aqueous layer extracted with EtOAc (20 mL). The combined organic layer was washed with saturated sodium bicarbonate (20 mL) and dried over sodium sulfate. After removal of solvent, the residue was purified by flash chromatography (10:1=DCM:MeOH) to give [1-benzyl-2-oxo-2-(4-pyrido[2,3-d]pyrimidin-4-yl-piperazin-yl)-ethyl-carbamic acid tert-butyl ester as white foam solid (0.392 g, 58.9%). 1H NMR (CDCl3, 400 MHz) δ 9.11 (br, 1H), 8.92 (s, 1H), 8.15 (d, 1H), 7.40 (m, 1H), 7.20-7.33 (m, 5H), 5.42 (m, 1H), 4.85 (m, 1H), 3.78-3.82 (m, 2H), 3.61-3.70 (m, 2H), 3.50-3.58 (m, 2H), 3.15-3.20 (m, 1H), 3.08-3.12 (m, 2H), 1.42 (s, 9H). Rt 2.23 min. MS (ESI+) [M+H]+463.

Provenance & Evidence