Triphenylphosphine → HCID 59540949, compound

Participants

Reaction Steps

A flask was charged with 1-[2-(3-hydroxy-5-pyrrolidin-1-yl-phenyl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one (140 mg, 0.28 mmol), 2-methylsulfanyl-ethanol (reagent A, 0.03 ml, 0.34 mmol), triphenylphosphine (reagent B, 89 mg, 0.34 mmol). THF (1.5 ml) was added and the mixture cooled (ice bath) under nitrogen atmosphere. Diisopropyl azodicarboxylate (reagent C, 0.07 ml, 0.34 mmol) was added via syringe and the material was warmed to ambient. After 1 hour a further 1.2 equivalents each of reagents A, B and C were added. After 2 hours repeat. The mixture was stirred overnight. The crude was loaded onto 2 preparative TLC plates eluting with 20% EtOAc in hexanes. The product band was collected providing 2,2-dimethyl-1-[2-[3-(2-methylsulfanyl-ethoxy)-5-pyrrolidin-1-yl-phenyl]-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-propan-1-one, 82 mg as a yellow viscous oil.

Provenance & Evidence