Piperidine → HCID 67269263, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 1.6 g (7.75 mmol) 6-(4-ethyl-piperazin-1-yl)-pyrimidin-4-ylamine (intermediate 4), 2.03 g (9.3 mmol) di-tert-butyl dicarbonate and 1.17 g (11.6 mmol) NEt3 in 30 mL DCM was stirred at 50° C. in a sealed tube for 16 h. After evaporation of all volatiles the residue was purified with flash column chromatography on silica. The combined product fractions were evaporated to dryness to yield [6-(4-ethyl-piperazin-1-yl)-pyrimidin-4-yl]-carbamic acid tert-butyl ester. MS(m/e): 308.4 (MH+). A mixture of 28 mg (0.09 mmol) [6-(4-ethyl-piperazin-1-yl)-pyrimidin-4-yl]-carbamic acid tert-butyl ester, 0.18 mL (0.36 mmol) 2M AlMe3 solution in toluene and 30 mg (0.36 mmol) piperidine in 1 mL toluene were heated to 120° C. for 16 h. After removal of all volatiles under reduced pressure the residue was taken up in methanol/NEt3 and subjected to preparative HPLC purification on reversed phase eluting with a gradient of acetonitrile/water (0.05% triethylamine). The combined product fractions were evaporated to dryness to yield 5.3 mg (18%) of the title compound. MS (m/e): 319.1 (MH+).

Provenance & Evidence