Methyl iodide → 2-Amino-6-methylthio-9-(2-hydroxyethoxymethyl)purine

HRID 2050025Notes

Reaction equation

HRID 2050025 reaction equation
[OH:1][CH2:2][CH2:3][O:4][CH2:5][N:6]1[CH:14]=[N:13][C:12]2[C:11](=[S:15])[NH:10][C:9]([NH2:16])=[N:8][C:7]1=2.[CH3:17]I>CO>[NH2:16][C:9]1[N:8]=[C:7]2[C:12]([N:13]=[CH:14][N:6]2[CH2:5][O:4][CH2:3][CH2:2][OH:1])=[C:11]([S:15][CH3:17])[N:10]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 178508225HCID 178508225, compound

Product 1

HCID 205176832-Amino-6-methylthio-9-(2-hydroxyethoxymethyl)purineYield 38%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture 9-(2-Hydroxyethoxymethyl)thioguanine (0.7 g), methyl iodide (0.2 ml), Dowex HCO3- resin (1.7 g) and methanol (200 ml) was stirred overnight at room temperature. The resin was removed by filtration, washed with methanol and the combined filtration evaporated, and the residue recrystallized from isopropanol and then from acetone to give 2-amino-6-methylthio-9-(2-hydroxyethoxymethyl)purine, m.p. 188°-191° C. in 38% yield.

Workup

  1. customThe resin was removed by filtration
  2. washwashed with methanol
  3. filtrationthe combined filtration
  4. customevaporated
  5. customthe residue recrystallized from isopropanol

Sources & evidence

ORD record
ord-b09c71d2ebbb4a4ea03a66db8886156c
Source dataset
uspto-grants-1980_04
Patent number
US04199574

Reaction notes

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