Potassium Carbonate → [4-(5-Carbamoylpyrazin-2-yloxy)benzyl]phenethylcarbamic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

Take up 5-chloropyrazine-2-carboxamide (0.0527 g, 0.334 mmol), (4-hydroxybenzyl)phenethylcarbamic acid tert-butyl ester (Example 380, Part B) (0.110 g, 0.334 mmol) and K2CO3 (0.116 g, 0.836 mmol) in DMF (0.80 mL). Heat at 140° C. for 21.5 hours. Concentrate the reaction mixture then purify by flash chromatography, eluting with 50% ethyl acetate in hexanes to give the title compound (0.019 g, 12.7%): MS ES+ 448.8 (M+H)+, base peak MS ES+ 392.8 (M−C(CH3)3)+; HPLC [YMC-Pack Pro C-18 (150×4.6 mm, S-5 microm), 0.1% TFA/acetonitrile in 0.1% TFA/water at 1.0 mL/min, 30-99% over 19 min], tR=14.8 min, 100% purity.

Provenance & Evidence