Ammonium Sulfate → 1-(3-O-Acetyl-5-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-4-amino-5-chloro-2(1H)-pyrimidinone

HRID 2057579Notes

Reaction equation

HRID 2057579 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].[Cl:22][C:23]1[C:24]([N:34]([Si](C)(C)C)[Si](C)(C)C)=[N:25][C:26](=[O:33])[N:27]([Si](C)(C)C)[CH:28]=1.ClC1C(N)=NC(=O)NC=1.S([O-])([O-])(=O)=O.[NH4+].[NH4+]>C(Cl)Cl.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:27]2[CH:28]=[C:23]([Cl:22])[C:24]([NH2:34])=[N:25][C:26]2=[O:33])[C@H:6]1[F:21])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 6097028Ammonium SulfateHCID 9975824HCID 9975824, compoundHCID 70471483HCID 70471483, compoundHCID 178509020HCID 178509020, compound2×

Product 1

HCID 542677591-(3-O-Acetyl-5-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-4-amino-5-chloro-2(1H)-pyrimidinone

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 13838HexamethyldisilazaneSolvent

Procedure

To a solution of 3-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-D-arabinofuranosyl bromide (3.6 g, 0.01 mol) in methylene chloride (50 ml) is added a methylene chloride solution of 5-chloro-tris(trimethylsilyl)cytosine [prepared from 4.3 g, 0.03 mol. of 5-chlorocytosine as follows: a mixture of 5-chlorocytosine and 5-15 mg of ammonium sulfate in 43 ml of hexamethyldisilazane is heated to reflux until a clear solution is obtained. The excess hexamethyldisilazane is removed by evaporation in vacuo and the residue is dissolved in 25 ml of methylene chloride]. The mixture is stirred for 5 days at room temperature. Methanol (7 ml) is added to the reaction mixture, and the suspension is filtered through a Celite pad which is thoroughly washed with methylene chloride. The combined filtrate and washings are evaporated to dryness in vacuo and the residue is crystallized from ethanol to give 860 mg of 1-(3-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-chlorocytosine, m.p. 233°.

Workup

  1. customprepared from 4.3 g, 0.03 mol
  2. temperatureis heated
  3. temperatureto reflux until a clear solution
  4. customis obtained
  5. customThe excess hexamethyldisilazane is removed by evaporation in vacuo
  6. dissolutionthe residue is dissolved in 25 ml of methylene chloride]
  7. additionMethanol (7 ml) is added to the reaction mixture
  8. filtrationthe suspension is filtered through a Celite pad which
  9. washis thoroughly washed with methylene chloride
  10. customThe combined filtrate and washings are evaporated to dryness in vacuo
  11. customthe residue is crystallized from ethanol

Sources & evidence

ORD record
ord-e795043d6de342278e784d4c3ceee6e3
Source dataset
uspto-grants-1980_07
Patent number
US04211773

Reaction notes

Loading…