Sodium → HCID 178521058, compound

HRID 223164Notes

Reaction equation

HRID 223164 reaction equation
C([O:4][C@H:5]1[C@H:9]([O:10]C(=O)C)[C@@H:8]([CH2:14][O:15]C(=O)C)[O:7][C@H:6]1[N:19]1[C:23]2[N:24]=[CH:25][NH:26][C:27](=[S:28])[C:22]=2[CH:21]=[CH:20]1)(=O)C.[Na]>CO>[C@@H:6]1([N:19]2[C:23]3[N:24]=[CH:25][NH:26][C:27](=[S:28])[C:22]=3[CH:21]=[CH:20]2)[O:7][C@H:8]([CH2:14][OH:15])[C@@H:9]([OH:10])[C@@H:5]1[OH:4]

Participants

4

Reactant 2

HCID 5360545SodiumHCID 178476349HCID 178476349, compound

Product 1

HCID 178521058HCID 178521058, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3.0 g of 7-β-D-arabinofuranosyl-3,7-dihydro-4H-pyrrolo[2,3d]-pyrimidine-4-one, eight ml of acetic anhydride, 150 ml of pyridine, and 50 mg of p-dimethylaminopyridine is stirred at room temperature for 24 hours, evaporated in vacuo, co-evaporated with xylenes, and distributed between ethyl acetate and water. The ethyl acetate layer is washed with saturated NaHCO3 and dried with MgSO4. Removal of the ethyl acetate provides 7-(2,3,5-tri-O-acetyl-β-D-arabinofuranosyl)-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one. This is dissolved in 150 ml of dry pyridine, treated with 8.8 g of phosphorus pentasulfide, and heated under reflux for 5 hours. The pyridine is removed in vacuo and the residue is treated with water. The precipitate is filtered, washed with water, and recrystallized from ethanol to afford 7-(2,3,5-tri-O-acetyl-β-D-arabinofuranosyl)-3,7-dihydro-4H-pyrrolo[2,3-]pyrimidine-4-thione. A solution of 5.0 g of 7-(2,3,5-tri-O-acetyl-β-D-arabinofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine-4-thione, 200 ml of methanol, and 54 mg of sodium methalate is heated under reflux for 2 hours and treated with IRC-50 ion exchange resin. The filtrate is evaporated in vacuo and the resulting residue is recrystallized from ethanol-water to provide 7-β-D-arabinofuranosyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidine-4-thione.

Workup

  1. temperatureunder reflux for 2 hours
  2. additiontreated with IRC-50 ion exchange resin
  3. customThe filtrate is evaporated in vacuo
  4. customthe resulting residue is recrystallized from ethanol-water

Sources & evidence

ORD record
ord-abb146357884451b9e3847f838fd8178
Source dataset
uspto-grants-1982_10
Patent number
US04352795

Reaction notes

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