2-Methyl-5-(trimethylstannyl)thiazole → HCID 86685318, compound

Participants

Reaction Conditions

Reaction Steps

A flask charged with 7-chloro-5-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidine (Preparation G; 0.200 g, 0.572 mmol) and 2-methyl-5-(trimethylstannyl)thiazole (0.165 g, 0.629 mmol) was evacuated and backfilled with argon before 4 mL of dioxane were added and argon was bubbled through for 5 minutes. Tris(dibenzylideneacetone)dipalladium (0.0523 g, 0.0572 mmol) and dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (0.0545 g, 0.114 mmol) were added, argon was bubbled through the reaction for 10 minutes. The reaction flask was sealed and heated to 100° C. with stirring for 2 hours. The reaction mixture was loaded directly onto a silica gel column pre-wetted and eluted with a gradient of 25-100% ethyl acetate with 1% ammonium hydroxide to afford 2-methyl-5-(5-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-7-yl)thiazole (0.196 g, 0.475 mmol, 83.1% yield). MS (apci) m/z=413.1 (M+H).

Provenance & Evidence