反应详情

温度

100 °C

A glass vial was charged with 2′-hydroxy-7′-(5-pyrimidinyl)spiro[1,3-oxazole-4,9′-xanthen]-2-amine (prepared as described in Example 3; 159 mg, 459 μmol), tetrabutylammonium iodide (84.8 mg, 230 μmol), cesium carbonate (374 mg, 1148 μmol), DMF (1.8 mL), and 1-bromo-2,2-dimethylpropane (175 μl, 1377 μmol). The vial was sealed and heated in a Biotage Initiator microwave reactor for 2 h at 100° C. Additional portions of tetrabutylammonium iodide (85 mg), cesium carbonate (180 mg), and 1-bromo-2,2-dimethylpropane (100 uL) were added. The vial was again heated in the microwave for 2 h at 100° C. The mixture was poured into water (10 mL) and extracted with EtOAc (3×10 mL). The combined organic extracts were dried over sodium sulfate, filtered, and evaporated. The residue was purified by chromatography on silica gel (eluting with 0-80% of a 90:10:1 DCM/MeOH/NH4OH mixture in DCM) to give 2′-(2,2-dimethylpropoxy)-7′-(5-pyrimidinyl)spiro[1,3-oxazole-4,9′-xanthen]-2-amine of a pale orange glass that solidified into an off-white solid. MS m/z=417.2 [M+H]+. Calc'd for C24H25N4O3: 417.2.

1. customThe vial was sealed
2. temperatureThe vial was again heated in the microwave for 2 h at 100° C
3. extractionextracted with EtOAc (3×10 mL)
4. dry with materialThe combined organic extracts were dried over sodium sulfate
5. filtrationfiltered
6. customevaporated
7. customThe residue was purified by chromatography on silica gel (eluting with 0-80% of a 90:10:1 DCM/MeOH/NH4OH mixture in DCM)