Diisopropylethylamine → HCID 178455280, compound

Participants

Reaction Steps

5-Benzyloxy-2-[1-(4-chlorophenyl)-cyclopentylmethyl]-6-hydroxypyrimidine-4-carboxylic acid (324) (150 mg, 0.34 mmol) and [2-(tert-butyl-dimethylsilanyloxy)-ethyl]-(tetrahydro-pyran-4-yl)-amine (8j) were taken up in dimethylformamide (3 ml). HATU (195.2 mg, 0.51 mmol) and N,N-diisopropylethylamine (110.4 mg, 0.86 mmol) were added at room temperature and the reaction mixture was stirred for 16 h (monitored by LC-MS). To the reaction, water was added (10 ml) and the mixture was stirred for 5 min. Thereafter, the aqueous mixture was extracted with ethyl acetate (2×15 ml) and 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]-(tetrahydro-pyran-4-yl)-amide (333) (130 mg, 56%) as a yellow sticky solid.

Provenance & Evidence