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

HRID 1974847Notes

Reaction equation

HRID 1974847 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-900b2ff93f7e402d8185b37ca1e08f46
Source dataset
uspto-grants-1994_02
Patent number
US05284837

Reaction notes

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