Reacción #537765

Ecuación de reacción

4-(4-fluoro-2-(tetrahydro-2H-pyran-4-yloxy)phenylamino)-5-methylthieno[2,3-d]pyrimidine-6-carboxamide

trifluoroacetic anhydride

→

title compound

Rendimiento 68.0%

4-(4-Fluoro-2-(tetrahydro-2H-pyran-4-yloxy)phenylamino)-5-methylthieno[2,3-d]pyrimidine-6-carbonitrile

Rendimiento 68.0%

Disolventes

DCM pyridine

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe reaction was quenched with ice
2. 2
   OtroThe mixture was partitioned between DCM (10 mL) and water (10 mL)
3. 3
   LavadoThe aqueous phase was washed with DCM (10 mL)
4. 4
   Secadothe combined organic layers dried (MgSO4)
5. 5
   Filtraciónfiltered
6. 6
   Concentraciónconcentrated in vacuo
7. 7
   OtroThe crude product was purified by flash column chromatography (DCM→49:1 DCM/MeOH)

Procedimiento

To a stirred suspension of 4-(4-fluoro-2-(tetrahydro-2H-pyran-4-yloxy)phenylamino)-5-methylthieno[2,3-d]pyrimidine-6-carboxamide (0.1 g, 0.25 mmol) in DCM/pyridine (2.5 mL; 4:1) was added trifluoroacetic anhydride (0.138 mL, 1.0 mmol) at 0° C. and the mixture stirred for 4 hours. The reaction was quenched with ice and adjusted to pH 7 with saturated sodium hydrogen carbonate solution. The mixture was partitioned between DCM (10 mL) and water (10 mL). The aqueous phase was washed with DCM (10 mL) and the combined organic layers dried (MgSO4) filtered and concentrated in vacuo. The crude product was purified by flash column chromatography (DCM→49:1 DCM/MeOH) to give the title compound as a pale yellow solid (0.065 g, 68%) after crystallisation from MeOH.

Fuente