Water → HCID 58009787, compound

Participants

Reaction Conditions

Reaction Steps

2-(Azidomethyl)-6-(5-methoxy-1-methyl-1H-indol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine (4.23 g, 9.12 mmol, Preparation #G.1) in THF (100 mL) was treated with triphenylphosphine (2.39 g, 9.12 mmol) and water (1.4 mL, 78 mmol). The mixture was heated at about 65° C. for about 4 h. The mixture was cooled to rt and concentrated under reduced pressure. The material was purified by flash chromatography on silica gel with 98:2 then 9:1 DCM/MeOH containing 2.5 vol % of a solution of 37% aqueous NH4OH to give (6-(5-methoxy-1-methyl-1H-indol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl)methanamine (2.32 g, 58%): LC/MS (Table 2, Method a) Rt=2.30 min; MS m/z 438 (M+H)+.

Provenance & Evidence