N-methylcyclopentanamine → HCID 57831045, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 1-[2-bromo-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one (0.051 g, 0.123 mmol) and methylcyclopentylamine (0.050 mL, 0.44 mmol) in 1 mL of N-methyl pyrrolidinone in a sealed tube was stirred at 200° C. for 20 h. Additional methylcyclopentylamine (0.100 mL, 0.88 mmol) was added, and the solution stirred at 200° C. for 3 d. After cooling, the dark orange solution was partitioned between 10 mL of ethyl acetate and 10 mL of a 10% citric acid solution. The organic layer was sequentially washed with three 10 mL portions of water and 10 mL of a sat. aq. NaCl solution, dried over MgSO4, filtered and concentrated to an orange oil. Column chromatography (0-20% EtOAc/hexanes) afforded 0.030 g (58%) of impure 1-[2-(cyclopentyl-methyl-amino)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one, which was used without further purification.

Provenance & Evidence