Sodium 2-methylbutan-2-olate → Tert-butyl 4-(4-(8-ethyl-4-methyl-7-oxo-6-(thiazol-2-yl)-7,8-dihydropyrido[2,3-d]pyrimidin-2-ylamino)phenyl)piperazine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

Acetato(2′-di-t-butylphosphino-1,1′-biphenyl-2-yl)palladium(II) (45 mg, 0.098 mmol) was added to pressure tube charged with 2-amino-8-ethyl-4-methyl-6-(1,3-thiazol-2-yl)pyrido[2,3-d]pyrimidin-7(8H)-one (141 mg, 0.490 mmol), tert-butyl-4-(4-iodophenyl)tetrahydro-1(2H)pyrazinecarboxylate (209 mg, 0.539 mmol), and sodium tert-pentoxide (135 mg, 1.23 mmol) in dry toluene (1.5 mL). The pressure was capped under nitrogen and heated to 70° C.). After 60 hours, the reaction was cooled to room temperature and filtered through a pad of Celite. The filtrate was purified on silica gel (1:1 hexanes:ethyl acetate) to provide the product, tert-butyl 4-(4-(8-ethyl-4-methyl-7-oxo-6-(thiazol-2-yl)-7,8-dihydropyrido[2,3-d]pyrimidin-2-ylamino)phenyl)piperazine-1-carboxylate (99 mg, 34% yield).

Provenance & Evidence