m-Chloroperbenzoic acid → HCID 44466731, compound

Participants

Reaction Steps

To a solution of 5-amino-8-methyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one (163 mg, 0.733 mmol) in DCM (200 mL) was added 3-chloroperoxybenzoic acid (77% max., 164 mg, 0.733 mmol) at RT and the resulting mixture was stirred for 1 h. The reaction mixture was then evaporated under reduced pressure and the residue was dissolved in anhydrous dimethyl sulfoxide (7.3 mL). To a portion of this solution (1.8 mL) was added TEA (0.13 mL, 0.90 mmol), followed by 4,4-difluorocyclohexylamine hydrochloride (62 mg, 0.36 mmol) at RT. The reaction mixture was stirred at 80° C. for 4.5 h and was then quenched with water. The resulting mixture was extracted twice with EtOAc (20 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered and evaporated under reduced pressure. The crude residue was purified by flash chromatography (from 0 to >10% of MeOH/DCM in 10 min.) to give 27 mg (49% yield) of 5-amino-2-(4,4-difluoro-cyclohexylamino)-8-methyl-8H-pyrido[2,3-d]pyrimidin-7-one as a yellow solid. MS=310 [M+H]+.

Provenance & Evidence