Diisopropylethylamine → HCID 178455278, compound

Participants

Reaction Steps

5-Benzyloxy-2-[1-(4-chlorophenyl)-cyclopentylmethyl]-6-hydroxypyrimidine-4-carboxylic acid (324) (150.0 mg, 0.34 mmol) and [2-(tert-butyl-dimethylsilanyloxy)-ethyl]-cyclopropyl-amine (8d) (110.4 mg, 0.51 mmol) were taken up in dimethylformamide (3 ml), HATU (123.3 mg, 0.41 mmol) and N,N-diisopropylethylamine (132.5 mg, 1.03 mmol) were added at room temperature and stirred for 16 h while silica thin layer chromatography was performed (40% ethyl acetate in hexane; Rf=0.4). To the reaction, water (10 ml) was added and stirred for 5 min and the aqueous mixture was extracted with ethyl acetate (2×15 ml). The combined extracts were washed with water (3×10 ml), dried and concentrated under reduced pressure. The obtained crude product was purified by normal silica gel column chromatography (100-200 mesh) using 30% ethyl acetate in hexane as mobile phase to get pure 5-benzyloxy-2-[1-(4-chlorophenyl)-cyclopentylmethyl]-6-hydroxypyrimidine-4-carboxylic acid [2-(tert-butyl-dimethylsilanyloxy)-ethyl]-cyclopropyl-amide (325) (120 mg, 55%) as a yellow sticky solid.

Provenance & Evidence