반응 #537765

반응 방정식

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

trifluoroacetic anhydride

→

title compound

수율 68.0%

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

수율 68.0%

용매

DCM pyridine

반응 조건

후처리

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

실험 절차

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.

출처