反应详情

Thiourea (0.28 g) was added to a refluxing solution of 2-amino-6-chloro-9-(2-benzoyloxyethoxymethyl)purine (1.27 g) in isopropanol (40 ml). The reaction mixture was heated at reflux for 11/2 hours and then chilled. 9-(2-benzoyloxyethoxymethyl)-thioguanine (0.58 g, m.p. 199°-202° C.) was removed by filtration. This was added to 40 ml of aqueous ammonia (about 7 N) and the mixture heated on a steam bath for 10 minutes and then stirred overnight at room temperature. The water and ammonia were removed in vacuo and the residue triturated with acetone and then with ether to remove benzamide. The remaining solid was recrystallized twice from water to give yellow flakes of 9-(2-hydroxyethoxymethyl)thioguanine (0.26 g, m.p. 251°-254° C.).

1. temperatureThe reaction mixture was heated
2. temperatureat reflux for 11/2 hours
3. temperaturechilled
4. custom9-(2-benzoyloxyethoxymethyl)-thioguanine (0.58 g, m.p. 199°-202° C.) was removed by filtration
5. additionThis was added to 40 ml of aqueous ammonia (about 7 N)
6. temperaturethe mixture heated on a steam bath for 10 minutes
7. customThe water and ammonia were removed in vacuo
8. customthe residue triturated with acetone
9. customwith ether to remove benzamide
10. customThe remaining solid was recrystallized twice from water