Sodium t-butoxide → HCID 178503400, compound

Participants

Reaction Steps

Following the procedure described for Example 44 (MethOD B6), using trans-N1-(6-fluorobenzo[d]thiazol-2-yl)cyclobutane-1,3-diamine, INTERMEDIATE 72 (0.454 g, 1.913 mmol), ethyl 2-(4-chloro-2-(methylthio)pyrimidin-5-yl)-2-methylpropanoate (0.550 g, 2.002 mmol), dicyclohexyl(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine (0.185 g, 0.344 mmol), tris(dibenzylideneacetone)dipalladium (0) (0.131 g, 0.143 mmol), sodium t-butoxide (0.460 g, 4.78 mmol) in dry dioxane (3 mL) afforded the title 7-(trans-3-((6-fluorobenzo[d]thiazol-2-yl)amino)cyclobutyl)-5,5-dimethyl-2-(methylthio)-5H-pyrrolo[2,3-d]pyrimidin-6(7H)-one (0.230 g, 0.535 mmol, 28.0% yield). m/z: 430.1 (M+1); 1H NMR (400 MHz, CHLOROFORM-d) δ: ppm 1.41 (s, 6H) 2.42-2.53 (m, 2 H) 2.61 (s, 3H) 3.38-3.53 (m, 2 H) 4.55-4.65 (m, 1 H) 5.15-5.27 (m, 1 H) 5.91 (br s, 1 H) 7.03 (td, J=9.0 Hz, 2.6 Hz, 1H) 7.32 (dd, J=8.2 Hz, 2.6 Hz, 1H) 7.49 (dd, J=8.9 Hz, 4.7 Hz, 1H) 8.12 (s, 1H).

Provenance & Evidence