Water → 2-(5-Iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-methylpropan-1-ol

Reaction equation

[BH4-].[Li+].[I:3][C:4]1[C:12]2[CH:11]=[N:10][CH:9]=[N:8][C:7]=2[N:6]([C:13]([CH3:19])([CH3:18])[C:14](OC)=[O:15])[CH:5]=1.O>C(O)C>[I:3][C:4]1[C:12]2[CH:11]=[N:10][CH:9]=[N:8][C:7]=2[N:6]([C:13]([CH3:19])([CH3:18])[CH2:14][OH:15])[CH:5]=1

Participants

Procedure

Lithium borohydride (32.3 mL, 64.6 mmol, 2.0 M in THF) was added to methyl 2-(5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-methylpropanoate (8.92 g, 25.9 mmol) (see Preparation 21) in ethanol (70 mL). The mixture was stirred at room temperature for 17 hours then water (70 mL) was added. The mixture was evaporated in vacuo then the residue was partitioned between DCM (250 mL) and water (50 mL). The aqueous phase was extracted with DCM:MeOH (90:10, 2×250 mL) and the combined organic phases were dried over magnesium sulfate and evaporated in vacuo to afford the title compound as an off-white solid in 100% yield, 8.20 g.