反应详情

温度

30 °C

5-Amino-3H-thiazolo[4,5-d]pyrimidin-2-one (107 mg, 0.64 mmol) was dissolved in DMF (4 mL) at ambient temperature. Sodium hydride (30 mg, 1.32 mmol) was added and the mixture was heated to 30° C. Stirring was continued for 0.5 h before 3-bromomethyl-pyridine hydrobromide (179 mg, 0.71 mmol) was added. The mixture was then heated to 75° C. and allowed to stir for 4 h. Upon completion, the reaction was allowed to cool to room temperature, then concentrated. Water (12 mL) was added. The resulting mixture was diluted with H2O (12 mL), then extracted with ethyl acetate (3×5 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated. The crude material was purified by column chromatography (SiO2, 20-50% EtOAc—CH2Cl2) to generate 90 mg (54%) of 54 as a white solid: 1H NMR (400 MHz, DMSO-d6) δ 8.59 (s, 1H), 8.48 (d, J=3.6, 1H), 8.32 (s, 1H), 7.71 (d, J=8.4, 1H), 7.36 (m, 1H), 6.86 (s, 2H), 5.04 (s, 2H); [M+H]+ 260.1.

1. additionwas added
2. temperatureThe mixture was then heated to 75° C.
3. stirringto stir for 4 h
4. temperatureto cool to room temperature
5. concentrationconcentrated
6. additionWater (12 mL) was added
7. additionThe resulting mixture was diluted with H2O (12 mL)
8. extractionextracted with ethyl acetate (3×5 mL)
9. washThe combined organic layers were washed with brine
10. dry with materialdried over Na2SO4
11. filtrationfiltered
12. concentrationconcentrated
13. customThe crude material was purified by column chromatography (SiO2, 20-50% EtOAc—CH2Cl2)