反应详情

温度

0 °C

To a solution of 5-(benzyloxy)-2-((1-(4-chlorophenyl)cyclopentyl)methyl)-6-hydroxypyrimidine-4-carboxylic acid (28-02) (200 mg, 456 μmol, Eq: 1.00) and N-(2-(tert-butyldimethylsilyloxy)ethyl)aniline (46) (126 mg, 501 μmol, Eq: 1.1) in pyridine (2.00 ml) was added POCl3 (210 mg, 127 pμl, 1.37 mmol, Eq: 3.00) at −10° C. (ethylene glycol-dry-ice bath), then the reaction mixture was stirred at 0° C. for 2 hr. Ice cooled water was slowly added to the reaction mixture at 0° C., the reaction mixture was extracted with ethyl acetate, the organic layer was washed with aqueous saturated NaHCO3 solution, dried (MgSO4), concentrated, and chromatographed (silica gel, gradient 5 to 30% ethyl acetate-hexane) to obtain 5-(benzyloxy)-N-(2-(tert-butyldimethylsilyloxy)ethyl)-2-((1-(4-chlorophenyl)cyclopentyl)methyl)-6-hydroxy-N-phenylpyrimidine-4-carboxamide (47) (colorless oil, 287 mg, 427 μmol, 93.7% yield).

1. additionwas slowly added to the reaction mixture at 0° C.
2. extractionthe reaction mixture was extracted with ethyl acetate
3. washthe organic layer was washed with aqueous saturated NaHCO3 solution
4. dry with materialdried (MgSO4)
5. concentrationconcentrated
6. customchromatographed (silica gel, gradient 5 to 30% ethyl acetate-hexane)