Reaktion #1715284

Reaktionsgleichung

TIPSCl

2-(4-(1-methyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-3-yl)phenyl)propan-2-ol

NaH

→

2-(4-(1-methyl-6-(triisopropylsilyl)-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-3-yl)phenyl)propan-2-ol

Ausbeute 96.5%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGto stir at about −20° C. for about 1 h
2. 2
   Sonstigethe resulting mixture was partitioned between EtOAc (100 mL) and water (50 mL)
3. 3
   SonstigeThe layers were separated
4. 4
   Extraktionthe aqueous phase was extracted with EtOAc (3×25 mL)
5. 5
   WaschenThe combined organic phases were washed with saturated aqueous NaCl solution (100 mL)
6. 6
   Trocknendried over Na2SO4
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated in vacuo

Vorschrift

To a solution of 2-(4-(1-methyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-3-yl)phenyl)propan-2-ol (1.03 g, 3.36 mmol; Example #N.1.50) in THF (32 ml) at about −20° C. was added NaH (0.148 g, 3.70 mmol). The mixture was allowed to stir at about −20° C. for about 20 min. TIPSCl (0.790 ml, 3.70 mmol) was added and the resulting solution was allowed to stir at about −20° C. for about 1 h. The mixture was treated with 15 mL of an ice cold saturated aqueous NaCl solution and the resulting mixture was partitioned between EtOAc (100 mL) and water (50 mL). The layers were separated and the aqueous phase was extracted with EtOAc (3×25 mL). The combined organic phases were washed with saturated aqueous NaCl solution (100 mL), dried over Na2SO4, filtered, and concentrated in vacuo to give 2-(4-(1-methyl-6-(triisopropylsilyl)-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-3-yl)phenyl)propan-2-ol (1.5 g, 96%). LC/MS (Table 2, Method h) Rt=2.28 min; MS m/z 463 (M+H)+.

Quelle