Methanol → HCID 118093616, compound

Participants

Reaction Steps

Combine tert-butyl N-[[4-(6-cyano-2-methyl-pyrimidin-4-y)oxyphenyl]methylsulfonyl]-N-methyl-carbamate (400 mg, 0.96 mmol), triethylamine (290 mg, 2.9 mmol), MeOH (20 mL), and EtOAc (20 mL) in a PARR reactor. Add 5% palladium on carbon (203 mg, 0.096 mmol). Seal the PARR reactor and pressurize it with hydrogen (345 kPa). Shake the reactor at ambient temperature for 17 hours. Depressurize and open the reactor. Add an additional amount of 5% palladium on carbon (200 mg, 0.094 mmol); re-pressurize the reactor with hydrogen (414 kPa) and shake the reactor for an addition 17 hours while maintaining it at ambient temperature. Depressurize and open the reactor. Filter the contents through diatomaceous earth, and concentrate the filtrate under reduced pressure to provide a residue. To purify, add toluene and concentrate under reduced pressure to provide an orange-red residue. Repeat the toluene addition and removal 3 times to provide the title compound as a pink solid (0.57 g, 98.8%, 70% pure). MS (m/z): 423 (M+1).

Provenance & Evidence