Pyridine → 9-(4-Acetoxy-2-acetoxymethylbutyl)guanine

HRID 864994Notes

Reaction equation

HRID 864994 reaction equation
[OH:1][CH2:2][CH2:3][CH:4]([CH2:17][OH:18])[CH2:5][N:6]1[CH:14]=[N:13][C:12]2[C:11](=[O:15])[NH:10][C:9]([NH2:16])=[N:8][C:7]1=2.[C:19](OC(=O)C)(=[O:21])[CH3:20].N1[CH:31]=[CH:30]C=CC=1.CN(C)C=[O:35]>>[C:19]([O:1][CH2:2][CH2:3][CH:4]([CH2:17][O:18][C:30](=[O:35])[CH3:31])[CH2:5][N:6]1[CH:14]=[N:13][C:12]2[C:11](=[O:15])[NH:10][C:9]([NH2:16])=[N:8][C:7]1=2)(=[O:21])[CH3:20]

Participants

5

Reactant 4

HCID 1049PyridineHCID 6228DimethylformamideHCID 7918Acetic AnhydrideHCID 1354364559-(4-Hydroxy-2-(hydroxymethyl)butyl)guanine

Product 1

HCID 1357952119-(4-Acetoxy-2-acetoxymethylbutyl)guanineYield 69%

Procedure

A mixture of 9-(4-hydroxy-2-hydroxymethylbutyl)guanine (0.50 g, 2.0 mmol), acetic anhydride (1.02 g, 10.0 mmol), pyridine (1.11 g, 14.0 mmol), and dry N,N-dimethylformamide (25 ml) was stirred at room temperature for 13 days and then evaporated to dryness in vacuum. The crystalline residue was heated with 10 ml of water and lyophilized and recrystallized from water to give 0.468 g (69%) of 9-(4-acetoxy-2-acetoxymethylbutyl)guanine.

Workup

  1. customevaporated to dryness in vacuum
  2. temperatureThe crystalline residue was heated with 10 ml of water
  3. customrecrystallized from water

Sources & evidence

ORD record
ord-49568edd424b4c8a9a76da75f7cbe508
Source dataset
uspto-grants-1996_10
Patent number
US05565461

Reaction notes

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