1,2-Diaminocyclohexane → HCID 131734379, compound

Participants

Reaction Steps

tert-Butyl (3R)-3-[[5-(4-chloro-1,3-benzothiazol-2-yl)-6-methoxy-2-(morpholin-4-yl)pyrimidin-4-yl]amino]piperidine-1-carboxylate (200 mg, 0.36 mmol, 1.00 equiv), cyclohexane-1,2-diamine (112.9 mg, 0.99 mmol, 3.00 equiv), NaOBu-t (63.4 mg, 0.66 mmol, 2.00 equiv), tris(dibenzylideneacetone)dipalladium (30.2 mg, 0.03 mmol, 0.10 equiv) and O-biphenyl(t-Bu)2P (11.8 mg, 0.04 mmol, 0.12 equiv) in toluene (12.0 mL) were dissolved in dioxane (2 mL) and heated to reflux for 18 h. The mixture was cooled to room temperature and concentrated. The crude product was purified by flash chromatography on silica gel, eluting with a mixture of 6-50% ethyl acetate in petroleum ether (15:1-2:1) to provide the title compound as a yellow solid. MS, m/z:[M+H]+ (ESI): 639.

Provenance & Evidence