Cyanuric chloride → HCID 11045887, compound

Participants

Reaction Steps

A stirred solution of 5.3 g (29.0 mmol) of cyanuric chloride in 200 mL of DCM was cooled to −10° C. A solution of 5.3 g (29.0 mmol, 1.0 equiv.) of N-BOC piperazine and 6.2 g (29.0 mmo, 1.0 equiv.) of Proton Sponge® in 40 mL of DCM was then added dropwise over 20 min. to the cyanuric chloride solution. The resulting mixture was allowed to warm to RT and stirred 2 h. The reaction mixture was quenched by pouring into 150 mL of a 5% aqueous citric acid solution and extracted with DCM (2×100 mL). The organic layers were combined, dried (MgSO4), and concentrated in vacuo. Purification of the residue by silica gel flash column chromatography eluting with hexanes/EtOAc 3:1 afforded 8.6 g (85%) of the title compound as a white solid: 1H NMR (CDCl3, 400 MHz) δ 3.86 (m, 4H), 3.49 (m, 4H), 1.42 (s, 9H); low resolution MS (ES+) m/e 335 (MH+);TLC (hexanes/EtOAc 20:1) Rf=0.10. Intermediate 2: tert-butyl-4-{4-chloro-6-[[3-(4-chlorophenyl)propyl](methyl)amino]-1,3,5-triazin-2-yl}-1-piperazinecarboxylate.

Provenance & Evidence