Phosphorus oxychloride → HCID 178436101, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-(benzyloxy)-2-((1-(4-chlorophenyl)cyclopentyl)methyl)-6-hydroxypyrimidine-4-carboxylic acid (28-02) (170 mg, 387 μmol, Eq: 1.00) and 2-(tert-butyldimethylsilyloxy)-N-(1-phenylethyl)ethanamine (34) (108 mg, 387 μmol, Eq: 1.00) in pyridine (2.00 ml) was added POCl3 (178 mg, 108 μl, 1.16 mmol, Eq: 3.00) at −10° C. (ethylene glycol-dry-ice bath), then the reaction mixture was stirred at 0° C. for 2 hr. The reaction mixture was quenched with ice cooled-water (0.5 ml), 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-(1-phenylethyl)pyrimidine-4-carboxamide (35) (220 mg, 314 μmol, 81.1% yield).

Provenance & Evidence