Methanol → HCID 12136958, compound

HRID 1760223Notes

Reaction equation

HRID 1760223 reaction equation
[NH2:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1)[N:6]2[C:11]1[CH:12]=[CH:13][C:14]([OH:17])=[N:15][CH:16]=1.[CH3:24][O-].[Na+].CI.CO>O.C(OCC)(=O)C.O1CCCC1>[NH2:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1)[N:6]2[C:11]1[CH:12]=[CH:13][C:14](=[O:17])[N:15]([CH3:24])[CH:16]=1

Participants

8

Reactant 4

HCID 887MethanolHCID 6328Methyl iodideHCID 10942334Sodium MethoxideHCID 178508634HCID 178508634, compound

Product 1

HCID 12136958HCID 12136958, compoundYield 58%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 150 mg of 5-[6-amino-8-(2-pyridyl)-9H-9-purinyl ]-2-pyridinol, 133 mg of sodium methoxide and 306 μL methyl iodide in 20 mL mixture of methanol and tetrahydrofuran in a ratio of 1/1 was stirred at room temperature for 2 hours and 35 minutes and then at 60° C. for 45 minutes. Ethyl acetate and water were added to the reaction mixture, and this mixture was extracted once with ethyl acetate. The organic layer was washed with brine, and the whole aqueous layer was extracted twice with ethyl acetate. The whole organic layer was dried over magnesium sulfate and filtered, and from the resulting residues, the solvent was evaporated, to give 90 mg of the title compound as brown crystals (58% y.).

Workup

  1. extractionthis mixture was extracted once with ethyl acetate
  2. washThe organic layer was washed with brine
  3. extractionthe whole aqueous layer was extracted twice with ethyl acetate
  4. dry with materialThe whole organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. customfrom the resulting residues, the solvent was evaporated

Sources & evidence

ORD record
ord-7643f6ede4e144cca6cd698d3c901115
Source dataset
uspto-grants-2005_01
Patent number
US06841549B1

Reaction notes

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