Acetic Anhydride → HCID 178476387, compound

HRID 2354848Notes

Reaction equation

HRID 2354848 reaction equation
[OH:1][C:2]1[N:3]([CH2:16][C:17]2[CH:18]=[N:19][C:20]([CH3:23])=[CH:21][CH:22]=2)[C:4]2[C:9]([N:10]=1)=[C:8]([NH2:11])[N:7]=[C:6]([NH:12][CH2:13][CH2:14][OH:15])[N:5]=2.[C:24](OC(=O)C)(=[O:26])[CH3:25].C(=O)([O-])O.[Na+]>N1C=CC=CC=1>[C:24]([O:15][CH2:14][CH2:13][NH:12][C:6]1[N:5]=[C:4]2[C:9]([N:10]=[C:2]([OH:1])[N:3]2[CH2:16][C:17]2[CH:18]=[N:19][C:20]([CH3:23])=[CH:21][CH:22]=2)=[C:8]([NH2:11])[N:7]=1)(=[O:26])[CH3:25]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 178425471HCID 178425471, compound

Product 1

HCID 178476387HCID 178476387, compoundYield 12.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To 8-hydroxy-2-(2-hydroxyethylamino)-9-{(6-methyl-3-pyridyl)methyl}adenine (100 mg, 0.32 mmol) prepared by Comparative example 10 in pyridine (1 ml) was added under ice cooling acetic anhydride (0.033 ml, 0.35 mmol), and the mixture was stirred for 3 hours. To the reaction mixture was added sodium hydrogen carbonate solution, and the mixture was extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate and concentrated. The residue was purified by preparative thin-layer chromatography to give the captioned compound (14 mg, 0.039 mmol, yield: 12%) as a white solid.

Workup

  1. additionwas added under ice
  2. extractionthe mixture was extracted with chloroform
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by preparative thin-layer chromatography

Sources & evidence

ORD record
ord-8c28fbe4f7014aed91c0bb7fbed45dc3
Source dataset
uspto-grants-2010_07
Patent number
US07754728B2

Reaction notes

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