[I:1][C:2]1[C:10]2[CH:9]=[N:8][CH:7]=[N:6][C:5]=2[N:4]([C:11]([CH3:15])([CH3:14])[CH2:12][OH:13])[CH:3]=1.[H-].[Na+].[CH3:18]I>C1COCC1>[I:1][C:2]1[C:10]2[CH:9]=[N:8][CH:7]=[N:6][C:5]=2[N:4]([C:11]([CH3:15])([CH3:14])[CH2:12][O:13][CH3:18])[CH:3]=1An anhydrous THF (100 mL) solution of 2-(5-Iodo-pyrrolo[2,3-d]pyrimidin-7-yl)-2-methyl-propan-1-ol (Preparation 22) (32 g, 100.91 mmol) was added slowly to a suspension of NaH (60% in paraffin oil, 2.98 g, 121.13 mmol) in anhydrous THF (200 mL) at 00° C. under nitrogen. The mixture was warmed to room temperature and stirred for another 30 minutes and again cooled to 00° C. and methyl iodide (19 mL, 302.82 mmol) was added drop wise. The reaction mixture was stirred at room temperature for 2 hours, quenched with aqueous saturated ammonium chloride, and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulphate and evaporated to dryness in vacuo. The crude material was purified by column chromatography on silica (100-200 mesh, gradient of hexane:EtOAc 100:0 to 70:30) to afford the title compound as a yellow sticky solid in 22% yield, 7.5 g.
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