Hydrochloric Acid → HCID 67269365, compound

Participants

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 31 mg (0.1 mmol) [6-(4-ethyl-piperazin-1-yl)-pyrimidin-4-yl]-carbamic acid tert-butyl ester, 20 mg (0.15 mmol) cyclopentanecarbonyl chloride and 30 mg (0.3 mmol) NEt3 in 2 mL DCM was shaken at room temperature for 6 h. Subsequently, 3 mL HCl (4N) was added, the mixture was shaken at 50° C. for 4 h and all volatiles removed 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 20 mg (66%) of the title compound as white solid. MS (m/e): 344.1 (MH+).

Provenance & Evidence