ChemicalBook CAS DataBase List 2'-O-(2-Methoxyethyl)cytidine

2'-O-(2-Methoxyethyl)cytidine synthesis

4synthesis methods

Product Name:2'-O-(2-Methoxyethyl)cytidine
CAS Number:223777-16-0
Molecular formula:C12H19N3O6
Molecular Weight:301.3

2'-O-(2-Methoxyethyl)uridine could be converted into the corresponding cytidine derivative (2'-O-(2-Methoxyethyl)cytidine) by the 4-nitrophenylation[1]. 2'-O-(2-Methoxyethyl)uridine, l-methylpyrrolidine, chlorotrimethylsilane and dry acetonitrile were stirred together at rt. After 1 h, the reaction mixture was cooled to 0 ℃, and trifluoroacetic anhydride was added dropwise over 5 min. After a further period of 30 rain at 0 ℃, 4-nitrophenol was added to the stirred reactants which were maintained at 0 °C. After 3 h, the products were poured into saturated aqueous sodium hydrogen carbonate, and the resulting mixture was extracted with dichloromethane. The combined organic layers were dried, and evaporated under reduced pressure. Concentrated aqueous ammonia was added to a stirred solution of the residue in dioxane, contained in a sealed flask that was then heated at 55°C for 24 h. The resulting yellow solution was concentrated under reduced pressure and the residue was evaporated with absolute ethanol. The products were fractionated by short column chromatography on silica gel and were evaporated under reduced pressure to give 2'-O-(2-Methoxyethyl)cytidine as an off-white solid.

223777-15-9 Synthesis

223777-15-9
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223777-16-0
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Yield:223777-16-0 84%

Reaction Conditions:

Stage #1: 2'-O-(2-methoxyethyl)uridinewith 1-Methylpyrrolidine;chloro-trimethyl-silane in acetonitrile at 20; for 1 h;
Stage #2: with trifluoroacetic anhydride in acetonitrile at 0; for 0.0833333 h;
Stage #3: with 4-nitro-phenol;sodium bicarbonate;ammonia;watermore than 3 stages;

Steps:

Preparation of 2'-O-(2-Methoxyethyl)cytidine

Preparation of 2'-O-(2-Methoxyethyl)cytidine 2'-O-(2-Methoxyethyl)uridine (6.05g, 20.0mmol), 1-methylpyrrolidine (20ml, 0.192mol), chlorotrimethylsilane (7.6ml, 59.9mmol) and dry acetonitrile (100ml) were stirred together at room temperature. After 1 hour, the reactants were cooled to 0°C (ice-water bath) and trifluoroacetic anhydride (7.1ml, 50.3 mmol) was added dropwise over 5 minutes. After a further period of 30 minutes at 0°C, 4-nitrophenol (8.35g, 60mmol) was added to the stirred reactants which were maintained at 0°C. After 3 hours, the products were poured into saturated aqueous sodium hydrogencarbonate (200ml), and the resulting mixture was extracted with dichloromethane (3 x 100ml). The combined organic layers were dried (MgSO4), and evaporated under reduced pressure. Concentrated aqueous ammonia (d 0.88, 20ml) was added to a stirred solution of the residue in dioxane (100ml), contained in a sealed flask that was then heated at 55°C for 24 hours. The resulting yellow solution was concentrated under reduced pressure, and the residue was evaporated with absolute ethanol (3 x 50ml). The products were fractionated by short column chromatography on silica gel: the appropriate fractions, which were eluted with dichloromethane-methanol-triethylamine (93:7:0.5 to 90:10:0.5 v/v) were evaporated under the reduced pressure to give the title compound as an off-white solid (5.07g 84%).

References:

EP1165584,2004,B1 Location in patent:Page 5

120-94-5 Synthesis