Aniline → HCID 86630086, compound

Participants

Reaction Steps

5-Chloro-2-(methylsulfonyl)-7-morpholinothiazolo[4,5-d]pyrimidine (1.0 eq) and aniline (1.0 eq) were heated in toluene at 60° C. for 15 h. Upon completion, reaction mixture was concentrated in vacuo and crude mixture was purified by silica gel chromatography to give intermediate 5-chloro-7-morpholino-N-phenylthiazolo[4,5-d]pyrimidin-2-amine which was reacted with 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine (2.0 eq) and bis(triphenylphosphine)palladium(II) dichloride (0.10 eq) in 1M KOAc aqueous solution (3.0 eq) and a 4× volume of acetonitrile and heated to 150° C. in a sealed microwave reactor for 10 min Upon completion, reaction mixture was concentrated in vacuo and crude mixture was purified by silica gel chromatography to give 146. MS (Q1) 406 (M+)

Provenance & Evidence