Reacción #69220

Ecuación de reacción

ammonium hydroxide

3-[4-(7-[2-(Trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]pentanedinitrile

ACN

lithium tetrafluoroborate

→

title compound

Rendimiento 91.3%

3-[4-(7H-Pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]pentanedinitrile

Rendimiento 91.3%

Disolventes

water

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroat rt
2. 2
   Otrogiving a cloudy solution
3. 3
   TemperaturaThe reaction was heated
4. 4
   Temperaturato reflux
5. 5
   TemperaturaAfter heating for 24 h the reaction
6. 6
   Temperaturacooled in an ice bath
7. 7
   Temperaturato warm to rt
8. 8
   Concentraciónconcentrated in vacuo
9. 9
   Otroto remove the ACN
10. 10
    Otrogiving a precipitate
11. 11
    OtroThe solids were collected
12. 12
    Lavadowashed with water
13. 13
    Otrodried

Procedimiento

3-[4-(7-[2-(Trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]pentanedinitrile (10.0 g, 0.0245 mol) was dissolved in ACN (200 mL, 3.83 mol) and water (20 g, 1.1 mol) at rt. To this lithium tetrafluoroborate (23.0 g, 0.245 mol) was added giving a cloudy solution. The reaction was heated to reflux and monitored by HPLC. After heating for 24 h the reaction was allowed to cool to rt and then cooled in an ice bath. To this, ammonium hydroxide (23 mL, 0.59 mol) was added slowly. The reaction was allowed to warm to rt. After stirring for 18 hs the reaction was diluted with water and concentrated in vacuo to remove the ACN, giving a precipitate. The solids were collected, washed with water and dried to give the title compound as an off-white solid (6.2 gm, 91%), LC/MS (M+H)+: 278, 1H NMR (DMSO-d6) δ 8.9(s, 1H), 8.72(s,1H), 8.43(s, 1H), 7.59(d, 1H), 6.92(d, 1H), 5.21(m,1H), 3.25(m, 4H).

Fuente