反应详情

A solution of 2-aminothieno[3,2-d]pyrimidin-4-yl 2-thienylmethanone (0.15 g, 0.57 mmol) in anhydrous pyridine (6 mL) under argon at 0° C. was treated with N,N-dimethylglycinyl chloride hydrochloride (0.11 g, 0.69 mmol), warmed to room temperature, refluxed for 16 h, cooled, concentrated in vacuo and partitioned between 3-M HCl (25 mL) and EtOAc (25 mL). The aqueous phase was washed with EtOAc (25 mL), filtered through celite, basified to pH 12 with 10% aqueous sodium hydroxide and the resulting precipitate filtered and dried in vacuo to give a brown solid which was purified by chromatography [SiO2; EtOAc-MeOH (100:0 to 85:15)]. The resulting yellow solid was dissolved in CH2Cl2 (5 mL), treated with 1-M HCl in ether (0.25 mL) and the resulting precipitate filtered and dried in vacuo to give the title compound (32 mg, 11%) as a yellow solid.

1. temperaturerefluxed for 16 h
2. temperaturecooled
3. concentrationconcentrated in vacuo
4. custompartitioned between 3-M HCl (25 mL) and EtOAc (25 mL)
5. washThe aqueous phase was washed with EtOAc (25 mL)
6. filtrationfiltered through celite
7. filtrationthe resulting precipitate filtered
8. customdried in vacuo
9. customto give a brown solid which
10. customwas purified by chromatography [SiO2; EtOAc-MeOH (100:0 to 85:15)]
11. dissolutionThe resulting yellow solid was dissolved in CH2Cl2 (5 mL)
12. additiontreated with 1-M HCl in ether (0.25 mL)
13. filtrationthe resulting precipitate filtered
14. customdried in vacuo