1-cyclohexyl-3-[7-isopropenyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-urea → 1-Cyclohexyl-3-[7-isopropyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-urea

Participants

Reaction Steps

The mixture of 1-cyclohexyl-3-[7-isopropenyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-urea (70 mg, 0.163 mmol) and Pd/C (17 mg, 0.016 mmol) in MeOH (1.6 mL) was shaked under 50 psi of H2 atmosphere overnight, filtered through a pad of celite, and washed with MeOH. The filtrate was concentrated to give crude 1-Cyclohexyl-3-[7-isopropyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-urea, which was dissolved in a solution of HCl in AcOH (1M, 1.6 mL). The reaction mixture was heated at 50° C. in the sealed tube for 2 hr, concentrated to dryness, dissolved in 2 mL of MeOH:H2O:Et3N 8:1:1 and ethylenediamine (0.11 mL, 1.63 mmol) was added. The reaction mixture was stirred overnight, concentrated and purified by SiO2 chromatography (8 g SiO2, DCM/MeOH 0 to 10% MeOH) to give 9 mg of 1-cyclohexyl-3-(7-isopropyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)-urea as a pale yellow solid (18% yield).

Provenance & Evidence