Lithium Hexamethyldisilazide → 5-amino-8-methyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one

Participants

Reaction Steps

To a solution of N-(5-cyano-2-methylsulfanyl-pyrimidin-4-yl)-N-methyl-acetamide (400 mg, 1.80 mmol) in THF (18 mL) was added a solution of lithium bis(trimethyl-silyl)amide (1.0 M in hexane, 7.2 mL, 7.20 mmol) at RT. The reaction mixture was stirred at RT for 1 h, then quenched with water (100 mL). The resulting mixture was extracted with EtOAc (100 mL); the organic layer dried over MgSO4, filtered and concentrated under reduced pressure. The crude residue was purified by flash chromatography (from 10 to >100% EtOAc/hexane in 10 min.) to give 163 mg (41% yield) of 5-amino-8-methyl-2-methylsulfanyl-8H-pyrido[2,3-d]-pyrimidin-7-one as a yellow solid.

Provenance & Evidence