C[Mg]Cl.[S:4]([N:14]1[C:18]2=[N:19][CH:20]=[C:21]([CH:23]=[O:24])[N:22]=[C:17]2[CH:16]=[CH:15]1)([C:7]1[CH:13]=[CH:12][C:10]([CH3:11])=[CH:9][CH:8]=1)(=[O:6])=[O:5].[NH4+].[Cl-].[CH3:27]COC(C)=O>C1COCC1.C(Cl)Cl>[S:4]([N:14]1[C:18]2=[N:19][CH:20]=[C:21]([CH:23]([OH:24])[CH3:27])[N:22]=[C:17]2[CH:16]=[CH:15]1)([C:7]1[CH:8]=[CH:9][C:10]([CH3:11])=[CH:12][CH:13]=1)(=[O:5])=[O:6]To a solution of methylmagnesium chloride (0.232 mL, 0.697 mmol) in THF (10 mL) at about −78° C. was added a solution of 5-tosyl-5H-pyrrolo[2,3-b]pyrazine-2-carbaldehyde (0.210 g, 0.697 mmol, Example #10, Step B) in DCM (10.0 mL). After about 10 min saturated aqueous NH4Cl was added to the reaction mixture. After warming to room temperature, EtOAc (30 mL) was added to the reaction mixture and the organic layer was separated, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The crude material was purified by silica gel chromatography eluting with 20-80% EtOAc/heptane to provide 1-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)ethanol (0.050 g, 23%) as a yellow oil. LC/MS (Table 2, Method a) Rt=2.04 min; MS m/z: 318 (M+H)+.
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