Triphosgene → HCID 86691221, compound

Participants

Reaction Steps

To a stirred solution of tert-butyl 4-(5-amino-6-(dibenzylamino)pyrimidin-4-ylamino)phenyl(methyl)carbamate (38) (5.4 g, 10.6 mmol) and TEA (2.14 g, 21.2 mmol) in dry DCM (60 mL) at 0° C. and under N2 atmosphere, was added a solution of triphosgene (1.07 g, 3.6 mmol) in dry DCM (30 mL) dropwise during 1 h. Stirring was continued for 1 h before the reaction was quenched with water (20 mL). The organic layer was separated, washed with water and brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by column chromatography (silica gel, 0 to 20% ethyl acetate in petroleum ether) to give tert-butyl 4-(6-(dibenzylamino)-8-oxo-7H-purin-9(8H)-yl)phenyl(methyl)carbamate (39) (4.2 g, 74%) as a light brown solid. LC-MS (ESI): m/z (M+1) 537.

Provenance & Evidence