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

HRID 2256820Notes

Reaction equation

HRID 2256820 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-9d5bf917a2204bdb95e78d07692d5cd3
Source dataset
uspto-grants-1997_08
Patent number
US05656617

Reaction notes

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