Sodium Hydroxide → 2-(4-amino-3-(1H-imidazol-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)acetic acid tert-butyl ester

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Reaction Steps

To a mixture of tert-Butyl 2-(4-amino-3-(4,5-dihydro-1H-imidazol-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)acetate (84 g, 0.265 mol) and DMSO (900 mL) in an ice water bath was added Dess-Martin periodinane (169.6 g, 0.4 mol) in portions while keeping the internal temperature below 25° C. The mixture was stirred for 2 h at room temperature and then poured into ice water (2 L) which contained 84 g of Na2S2O3. The mixture was adjusted to pH 12-14 with 3 N NaOH and filtered to give a solid, which was washed with water, re-suspended in ice-water (2 L), filtered, washed with water (500 mL), EtOAc (100 mL×2) and Et2O (100 mL×2), and dried in vacuo to give (2-(4-amino-3-(1H-imidazol-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)acetic acid tert-butyl ester (66.2 g, 80% yield). MS (ES) m/z 316.1 (M+H+).

Provenance & Evidence