反应详情

A solution of 8-chloro-3-ethyl-7-(2-propen-1-yl)-3,7-dihydro-1H-purine-2,6-dione (150 mg, 0.59 mmol) in anhydrous THF (4 ml) was treated with 3-[3-(phenylmethyl)-1,2,4-oxadiazol-5-yl]-1-propanol (154 mg, 0.71 mmol) and triphenylphosphine (200 mg, 0.76 mmol). DBAD (162 mg, 0.71 mmol) was added in one portion and the mixture was left to stir at rt, under nitrogen for 18 h. The mixture was degassed by high vacuum then Pd(PPh3)4 (68 mg, 0.059 mmol) and morpholine (515 μl, 5.9 mmol) were added. The mixture was left to stir at rt, under nitrogen, for 3 h. The mixture was partitioned between EtOAc and 2M HCl (aq). The organic layer was separated, washed with brine, dried (MgSO4) and concentrated by high vacuum. The crude material was purified by an aminopropyl SPE using MeOH to load the compound onto the column and wash through the impurities, then with 2% AcOH/MeOH to elute the compound. The UV active fractions were combined and concentrated by high vacuum. The product was further purified by MDAP. The product fractions were combined and concentrated to give the title compound as a white solid (61 mg, 25%).

1. waitthe mixture was left
2. customThe mixture was degassed by high vacuum
3. waitThe mixture was left
4. stirringto stir at rt, under nitrogen, for 3 h
5. customThe mixture was partitioned between EtOAc and 2M HCl (aq)
6. customThe organic layer was separated
7. washwashed with brine
8. dry with materialdried (MgSO4)
9. concentrationconcentrated by high vacuum
10. customThe crude material was purified by an aminopropyl SPE
11. washwash through the impurities
12. washwith 2% AcOH/MeOH to elute the compound
13. concentrationconcentrated by high vacuum
14. customThe product was further purified by MDAP
15. concentrationconcentrated