2-Chloro-4,6-dimethylpyrimidine → HCID 67342807, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 2-chloro-4,6-dimethylpyrimidine (5.00 g, 0.035 mol), 4-amino-1-Boc-piperidine (7.023 g, 0.035 mol), sodium tert-butoxide (5.055 g, 0.53 mol) in dioxane (120 mL) was added under an argon atmosphere palladium(II) acetate (0.630 g, 0.003 mol) and 2-(dicyclohexylphospino)biphenyl (1.966 g, 0.006 mmol). The reaction mixture was stirred for 5 hours at 130° C. It was diluted with ethyl acetate (400 mL) and washed with aqueous sodium carbonate (1M, 200 mL), water (200 mL) and brine (150 mL). The combined aqueous layers were extracted with ethyl acetate (400 mL) and the combined organic layers were dried over sodium sulfate. Concentration and purification by chromatography (SiO2, n-heptane/ethyl acetate=2:1 to 1:1) afforded the title compound (5.44 g, 51%) as an orange oil.

Provenance & Evidence