Phosphate → HCID 14258065, compound

HRID 1492475Notes

Reaction equation

HRID 1492475 reaction equation
[H-].[Li+].N[C:4]1[N:12]=[C:11]2[C:7]([NH:8][CH:9]=[N:10]2)=[C:6]([O:13][CH2:14][CH2:15][O:16][CH3:17])[N:5]=1.C(OC[C@@H]1[C@@H](COC(=O)C2C=CC=CC=2)CC2C(O2)C1)(=O)C1C=CC=CC=1.P([O-])([O-])([O-])=O>CN(C=O)C>[CH3:17][O:16][CH2:15][CH2:14][O:13][C:6]1[N:5]=[CH:4][N:12]=[C:11]2[C:7]=1[NH:8][CH:9]=[N:10]2

Participants

6

Reactant 4

HCID 1061PhosphateHCID 62714Lithium hydrideHCID 135468096-(2-Methoxyethoxy)-7H-purin-2-amineHCID 15280201HCID 15280201, compound

Product 1

HCID 14258065HCID 14258065, compoundYield 97.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In an atmosphere of argon gas, lithium hydride (4.8 mg, 0.6 mmole) was added to a suspension of 2-amino-6-(2-methoxyethoxy)-purine (354.4 mg, 1.69 mmoles) in anhydrous DMF (15 ml). After stirring the mixture at room temperature for one hour, (3S,4S)-3,4-bis(benzoyloxymethyl)-7-oxabicyclo[4.1.0]-heptane (310.4 mg, 0.85 mmole) was added, and the reaction was further continued at 140° C. for 1.5 hours. Then, while cooling the reaction mixture, 0.2M phosphate buffer solution (pH 7.0) was added thereto and the mixture was stirred for a while, and then the mixture was subjected to extraction with ethyl acetate. The extract solution was washed with water, washed with saturated aqueous solution of sodium chloride and dried on anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 2-amino-9-[1R,2R,4S,5S)-4,5-bis(benzoyloxymethyl)-2-hydroxycyclohexyl]-6-(2-methoxyethoxy)-purine (320 mg, Yield 65.6%).

Workup

  1. waitthe reaction was further continued at 140° C. for 1.5 hours
  2. additionwas added
  3. stirringthe mixture was stirred for a while
  4. extractionthe mixture was subjected to extraction with ethyl acetate
  5. washThe extract solution was washed with water
  6. washwashed with saturated aqueous solution of sodium chloride
  7. dry with materialdried on anhydrous sodium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-9ce804154ff7454d934ac38b9dc9831b
Source dataset
uspto-grants-1994_12
Patent number
US05374625

Reaction notes

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