4-chloro-5H,6H,7H-pyrrolo[2,3-d]pyrimidin-6-one → HCID 67265104, compound

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Reaction Steps

Combine potassium tert-butoxide (1.1 equiv; 321 μmol; 36.8 mg); IPrPd(acac)Cl (0.1 equiv; 29.2 μmol; 18.4 mg) and stir bar in 4 mL vial and purge with nitrogen for 10 min. Add anhydrous DME (2.5 mL) followed by 4-chloro-5,7-dihydro-pyrrolo[2,3-d]pyrimidin-6-one (1 equiv; 292 μmol; 50 mg); (R)-3-[4-(4-fluoro-3-trifluoromethyl-phenyl)-2-piperidin-4-yl-imidazol-1-yl]-1-methyl-piperidine (1.1 equiv; 321 μmol; 131.8 mg) and heat to 80° C. for 18 h. Dilute with 15 mL water, filter, and rinse with water. Dissolve purple solid in EA, wash with saturated sodium bicarbonate, brine, dry with anhydrous MgSO4, filter, evaporate and purify on 40 g silica gel with 2-10% MeOH/DCM to provide 99.6 mg (0.18 mmol; 63%) of the title compound as the free base. Dissolve in DCM, add 1 equiv 1M HCl in ether and evaporate to provide 101 mg of the title compound. MS (ES+): m/z=544 (M+H).

Provenance & Evidence