Triphenylphosphine → HCID 86590835, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-methyl-2-(trityl-amino)-thiazole-5-carboxylic acid (46 mg, 0.11 mmol) in dichloromethane (1.0 mL) at 25° C. was treated with triphenylphosphine (36 mg, 0.14 mmol). The reaction was cooled to 0° C. and was treated with N-chlorosuccinimide (18 mg, 0.14 mmol). This mixture was stirred at 0° C. for 30 min and then was warmed to 25° C. for 20 min. At this time, the reaction was treated with 3-cyclopropylmethyl-1-(2-fluoro-benzyl)-8-(4-methylamino-benzyl)-3,7-dihydro-purine-2,6-dione (100 mg, 0.23 mmol) and dichloromethane (2.5 mL). The reaction was stirred at 25° C. for 18 h. At this time, the reaction was treated with another portion of triphenylphosphine (36 mg, 0.14 mmol) and N-chlorosuccinimide (18 mg, 0.14 mmol). The reaction was stirred at 25° C. for 1 h. At this time, the reaction was diluted with dichloromethane (100 mL) and then washed with a saturated aqueous sodium bicarbonate solution (1×25 mL). The organics were dried over magnesium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230–400 mesh, 80:20 ethyl acetate/petroleum ether) afforded 4-methyl-2-(trityl-amino)-thiazole-5-carboxylic acid {4-[3-cyclopropylmethyl-1-(2-fluoro-benzyl)-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-ylmethyl]-phenyl}-methyl-amide (75.1 mg, 80.0%). The product was used without further purification or characterization.

Provenance & Evidence