p-Toluenesulfonic acid → HCID 46912889, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of (S)-1-ethyl-3-(4-(4-(3-methylmorpholino)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-yl)phenyl)urea (example 7) (200 mg, 0.48 mmol) and Et3N (133 μL, 0.95 mmol). in toluene (1.5 mL) was added 2,2,2-trifluoroethyltrichloromethane sulfonate (91 μL, 0.95 mmol) and DMSO (0.5 mL). The reaction mixture was heated to 100° C. overnight. The reaction was cooled, diluted with methanol and adsorbed onto a mp-TsOH cartridge (2.5 g, 3 mmol/g). The cartridge was rinsed with MeOH (3 column volumes) and the product was eluted with 7M NH3 in MeOH. The basic fractions were concentrated in vacuo and purified by prep HPLC (low pH) to give the desired product (2.1 mg, 0.9% yield).

Provenance & Evidence