Uracil → HCID 70466634, compound

HRID 1981882Notes

Reaction equation

HRID 1981882 reaction equation
[C:1]([O:4][C@@H:5]1[C@@H:9]([CH2:10][O:11][C:12](=[O:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[O:8][CH:7](Br)[C@H:6]1[F:21])(=[O:3])[CH3:2].C[Si](C)(C)[O:24][C:25]1[N:30]=[C:29]([O:31][Si](C)(C)C)[CH:28]=[CH:27][N:26]=1.N1C=CC(=O)NC1=O.S([O-])([O-])(=O)=O.[NH4+].[NH4+]>C[Si](C)(C)N[Si](C)(C)C>[C:1]([O:4][C@@H:5]1[C@@H:9]([CH2:10][O:11][C:12](=[O:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[O:8][C@@H:7]([N:26]2[CH:27]=[CH:28][C:29](=[O:31])[NH:30][C:25]2=[O:24])[C@H:6]1[F:21])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 1174UracilHCID 82640Pyrimidine, 2,4-bis[(trimethylsilyl)oxy]-HCID 6097028Ammonium SulfateHCID 9975824HCID 9975824, compound

Product 1

HCID 70466634HCID 70466634, compound

Reagents, catalysts & solvents 1

HCID 13838HexamethyldisilazaneSolvent

Procedure

A mixture of 3-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-D-arabinofuranosyl bromide (11.5 g) and 2,4-bis(trimethylsilyloxy)pyrimidine [prepared by refluxing a mixture of 5 g of uracil and 5-15 mg of ammonium sulfate in 25 ml of hexa-methyldisilazane until a clear solution is obtained followed by removal of the excess hexamethyldisilazane in vacuo] in 150 ml of methylene chloride is stirred for 5 days at room temperature. Methanol (5 ml) is added to the mixture and the suspension is filtered through a celite pad. The filtrate is evaporated in vacuo and the residue is triturated with diethyl ether to give a crude product which was recrystallized from ethanol to give pure 1-(3-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)uracil, 5.8 g, m.p. 179°-180°.

Workup

  1. customprepared
  2. temperatureby refluxing
  3. customis obtained
  4. customfollowed by removal of the excess hexamethyldisilazane in vacuo] in 150 ml of methylene chloride
  5. additionMethanol (5 ml) is added to the mixture
  6. filtrationthe suspension is filtered through a celite pad
  7. customThe filtrate is evaporated in vacuo
  8. customthe residue is triturated with diethyl ether
  9. customto give a crude product which
  10. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-ab768a11379a48508a2d6066f96645f5
Source dataset
uspto-grants-1986_06
Patent number
US04594339

Reaction notes

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