[CH2:1]([O:3][C:4]([C:6]1[C:14]2[C:9](=[N:10][CH:11]=[C:12]([C:15]3[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[C:17]([O:25][CH3:26])[CH:16]=3)[N:13]=2)[NH:8][C:7]=1[CH3:27])=[O:5])[CH3:2].[H-].[Na+].Cl[CH2:31][O:32][CH2:33][CH2:34][Si:35]([CH3:38])([CH3:37])[CH3:36]>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1[C:14]2[C:9](=[N:10][CH:11]=[C:12]([C:15]3[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[C:17]([O:25][CH3:26])[CH:16]=3)[N:13]=2)[N:8]([CH2:31][O:32][CH2:33][CH2:34][Si:35]([CH3:38])([CH3:37])[CH3:36])[C:7]=1[CH3:27])=[O:5])[CH3:2]To a solution of 6-Methyl-2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid ethyl ester (108 mg) in 3 ml of DMF was added 60% NaH. After stirring 15 minutes, (2-Chloromethoxy-ethyl)-trimethyl-silane (108 mg) was added and the mixture stirred at rt for 14 h. The mixture was partitioned between water and diethylether. The organic phase was concentrated and purified by flash chromatography (9:1 Hexanes:Ethyl acetate). Obtain 110 mg of 6-Methyl-2-(3,4,5-trimethoxy-phenyl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid ethyl ester.
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