Reaktion #1885925

Reaktionsgleichung

NaOH

tert-Butyl 2-(4-amino-3-(4,5-dihydro-1H-imidazol-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)acetate

Na2S2O3

Dess-Martin periodinane

→

2-(4-amino-3-(1H-imidazol-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)acetic acid

Lösungsmittel

DMSO

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe internal temperature below 25° C
2. 2
   Filtrationfiltered
3. 3
   Sonstigeto give a solid, which
4. 4
   Waschenwas washed with water
5. 5
   Filtrationfiltered
6. 6
   Waschenwashed with water (500 mL), EtOAc (100 mL×2) and Et2O (100 mL×2)
7. 7
   Sonstigedried in vacuo

Vorschrift

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 tent-butyl ester (66.2 g, 80% yield). MS (ES) m/z 316.1 (M+H+).

Quelle