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 (0.58 g, 1.3 mmol) in THF (15 mL) was treated with triphenylphosphine (0.335 g, 1.28 mmol) and water (0.150 mL, 8.33 mmol) then heated to about 70° C. for about 2 h. The mixture was cooled then concentrated in vacuo. The material was purified by silica gel chromatography eluting with 9:1 DCM/MeOH containing 2.5 vol % 37 wt %. aqueous ammonium hydroxide 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 (0.37 g, 68%): LC/MS (Table 2, Method a) Rt=2.11 min; MS m/z: 438 (M+H)+.

Provenance & Evidence