反应 #537765

反应方程式

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

trifluoroacetic anhydride

→

title compound

收率 68.0%

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

收率 68.0%

溶剂

DCM pyridine

反应条件

后处理

1. 1
   其他The reaction was quenched with ice
2. 2
   其他The mixture was partitioned between DCM (10 mL) and water (10 mL)
3. 3
   洗涤The aqueous phase was washed with DCM (10 mL)
4. 4
   干燥the combined organic layers dried (MgSO4)
5. 5
   过滤filtered
6. 6
   浓缩concentrated in vacuo
7. 7
   其他The crude product was purified by flash column chromatography (DCM→49:1 DCM/MeOH)

实验过程

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.

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