Reacción #962073

Ecuación de reacción

compound 138

Trifluoromethane sulfonic acid 3-(5-methyl-4-oxo-2-(1-[9-(2-trimethylsilanyl-ethoxymethyl)-9H-purin-6-ylamino]-ethyl)-4H-quinazolin-3-yl)-phenyl ester

DMF

→

compound 141

Rendimiento 66.0%

3-(5-methyl-4-oxo-2-{1-[9-(2-trimethylsilylethoxymethyl)-9H-purin-6-ylamino]ethyl}-4H-quinazolin-3-yl)benzonitrile

Rendimiento 66.0%

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroA 5-mL reaction
2. 2
   Otrovial equipped with a magnetic stirrer
3. 3
   OtroThe vial was purged with nitrogen
4. 4
   Temperaturathen cooled to ambient temperature
5. 5
   workup.ADDITIONpoured into a saturated aqueous sodium bicarbonate solution (25 mL)
6. 6
   ExtracciónThe resulting suspension was extracted with methylene chloride (3×20 mL)
7. 7
   Secadodried over sodium sulfate
8. 8
   Filtraciónfiltered
9. 9
   OtroConcentration of the filtrate followed by purification by column chromatography

Procedimiento

A 5-mL reaction vial equipped with a magnetic stirrer was charged with compound 138 (200 mg, 0.300 mmol), tetrakis(triphenylphosphine)pallasium (34.0 mg, 0.029 mmol), zinc cyanide (70 mg, 0.60 mmol) and anhydrous DMF (1 mL). The vial was purged with nitrogen, heated to 120° C. for 3.5 h then cooled to ambient temperature and poured into a saturated aqueous sodium bicarbonate solution (25 mL). The resulting suspension was extracted with methylene chloride (3×20 mL), and the organic extracts were combined, dried over sodium sulfate and filtered. Concentration of the filtrate followed by purification by column chromatography gave a 66% yield of compound 141 as a white solid. 1H NMR (CDCl3) δ (ppm) 8.30 (d, 1H, J=6.9 Hz), 7.58-8.02 (m, 7H), 7.30 (d, 1H, J=7.0 Hz), 5.60 (s, 2H), 5.07 (bs, 1H), 3.65 (m, 2H), 2.84 (s, 3H), 1.58 (d, 3H, J=6.7 Hz), 0.96 (m, 2H), 0.02 (s, 9H).

Fuente