Cyanuric chloride → N-[2-Benzyloxy-4-(4,6-dichloro-[1,3,5]triazin-2-ylamino)-phenyl]-acetamide

Participants

Reaction Steps

N-(4-Amino-2-benzyloxy-phenyl)-acetamide (399) (0.65 g, 2.54 mmol) and NaHCO3 (1.28 g, 15.24 mmol) were suspended in THF (100 mL) and chilled on a dry-ice/acetone bath. The cyanuric chloride (5) (0.465 g, 2.54 mmol) was dissolved in THF (4 mL) and added to the chilled solution. The ice-bath was removed and the mixture was stirred while warming to room temperature over a period of 45 minutes. TLC (Rf: 0.6 compared to Rf: 0.1 for compound 399 and Rf: 0.95 for compound 400 in 1:1 hexane/EtOAc, single spot) indicated complete reaction at this point. This reaction mixture was used directly in the next step without further purification or characterization.

Provenance & Evidence