Ammonia → HCID 67164793, Verbindung

Temperatur

0 °C

[(3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]methanol (0.400 g, 1.30 mmol) was dried by co-evaporation with pyridine, then suspended in dry pyridine (6.5 mL). TMSCl (0.330 mL, 2.60 mmol) was added and the mixture was stirred for 15 min. 4-Bromobenzoylchloride (0.342 g, 1.56 mmol) was added to the mixture and stirred for 2 h. The solution was cooled to 0° C. and 1 mL of H2O was added. After 5 min a 29% NH3 aq solution (0.847 mL) was added and the reaction mixture was stirred for 30 min while warming to r.t. The mixture was then concentrated and the residue was diluted with H2O (40 mL). The product was extracted with EtOAc (60 mL) and concentrated. The crude material was purified by flash chromatography (65 to 100% EtOAc/hexanes) to afford the title compound (0.305 g, 49%).

1. stirringstirred for 2 h
2. stirringthe reaction mixture was stirred for 30 min
3. temperaturewhile warming to r.t
4. concentrationThe mixture was then concentrated
5. additionthe residue was diluted with H2O (40 mL)
6. extractionThe product was extracted with EtOAc (60 mL)
7. concentrationconcentrated
8. customThe crude material was purified by flash chromatography (65 to 100% EtOAc/hexanes)

ORD-Eintrag

ord-bb4517ba29a748ebb3d3a55c4b8145aa

Quelldatensatz

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07951810B2