Uracil → HCID 57867363, compound

HRID 1516274Notes

Reaction equation

HRID 1516274 reaction equation
[NH:1]1[CH:8]=[CH:7][C:5](=[O:6])[NH:4][C:2]1=[O:3].C/C(/O[Si](C)(C)C)=N\[Si](C)(C)C.[C:21]([O:29][CH2:30][C@@H:31]1[C:35]([O:37][C:38](=[O:40])[CH3:39])([CH3:36])[C@:34]([F:42])([CH3:41])[CH:33](OC(=O)C)[O:32]1)(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.Cl[Sn](Cl)(Cl)Cl.C(=O)(O)[O-].[Na+]>C(#N)C>[C:21]([O:29][CH2:30][C@@H:31]1[C:35]([O:37][C:38](=[O:40])[CH3:39])([CH3:36])[C@:34]([F:42])([CH3:41])[CH:33]([N:1]2[CH:8]=[CH:7][C:5](=[O:6])[NH:4][C:2]2=[O:3])[O:32]1)(=[O:28])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

7

Reactant 5

HCID 1174UracilHCID 24287Tin tetrachlorideHCID 516892Sodium BicarbonateHCID 6913588N,O-bis(trimethylsilyl)acetamideHCID 57867364HCID 57867364, compound

Product 1

HCID 57867363HCID 57867363, compoundYield 61.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a stirred solution of uracil (about 0.30 g, 2.71 mmol) in acetonitrile (about 7 ml) was added N,O-Bis(trimethylsilyl)acetamide at room temperature (about 4 ml, 16.3 mmol) and refluxed for about 2 hours. To this added ((2R,4R)-3,5-diacetoxy-4-fluoro-3,4-dimethyl-tetrahydrofuran-2-yl)methyl benzoate (about 0.5 gm, 1.35 mmol) in acetonitrile (about 8 ml) drop wise at about 0° C., and added SnCl4 (about 0.2 ml, 2.03 mmol) and refluxed for about 15 hours, Completion of the reaction monitored by thin-layer chromatography and neutralized the reaction mixture with saturated sodium bicarbonate solution. Aqueous layer was extracted with ethyl acetate and the combined organic layers were washed with brine and dried over sodium sulphate. Concentration under reduced pressure and purification by silica gel column chromatography using 35% ethyl acetate/hexane as eluent furnished title compound (0.35 g) as a colorless solid. Yield: 61%; 1H-NMR: 1H NMR (300 MHz, CDCl3): δ 8.67 (s, 1H), 8.06-8.03 (m, 2H), 7.59-7.33 (m, 4H), 6.39 (d, 1H, J=22.8 Hz), 5.76, 5.55 (dd, 1H, J=2.1 Hz, J=2.4 Hz), 4.80-4.43 (m, 3H), 2.13 (s, 3H), 1.81 (d, 3H, J=2.4 Hz), 1.49 (d, 3H, J=23.4 Hz); ES Mass: [M+Na] 443 (100%); IR cm−: 3433, 2931, 2346, 1713, 1385, 1274, 952, 712; HPLC: 96%.

Workup

  1. temperaturerefluxed for about 2 hours
  2. temperaturerefluxed for about 15 hours
  3. extractionAqueous layer was extracted with ethyl acetate
  4. washthe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulphate
  6. concentrationConcentration
  7. customunder reduced pressure and purification by silica gel column chromatography

Sources & evidence

ORD record
ord-5fb33d647ce542a9a7fec784b92d7a2f
Source dataset
uspto-grants-2012_07
Patent number
US08227431B2

Reaction notes

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