Sodium Acetate → 5-Chloro-2-(4-methylsulfonylpiperazin-1-yl)-7-morpholinothiazolo[4,5-d]pyrimidine

Participants

Reaction Conditions

Reaction Steps

5-Chloro-2-(methylsulfonyl)-7-morpholinothiazolo[4,5-d]pyrimidine (1.0 eq) was dissolved in 1,2-dichloroethane (0.1 M). 1-methylsulfonylpiperazine (1.1 eq) and sodium acetate (1.1 eq) were added. The solution was stirred for 2 h at 70° C. and the solvent was removed in vacuo. The residue was purified by silica gel chromatography to give 5-chloro-2-(4-methylsulfonylpiperazin-1-yl)-7-morpholinothiazolo[4,5-d]pyrimidine. This intermediate, 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine (2.0 eq), trans-dichlorobis(triphenylphosphine)palladium(II) (0.10 eq), 1M KOAc (3.0 eq) and a 6× volume of acetonitrile were microwaved at 150° C. for 15 minutes. Upon completion, reaction mixture was concentrated in vacuo and crude mixture was purified by silica gel chromatography to give 145. MS (Q1) 477 (M+)

Provenance & Evidence