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

HRID 848096Notes

Reaction equation

HRID 848096 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-75eaadbae4f04da5b4251f3e64644afd
Source dataset
uspto-grants-1981_10
Patent number
US04294831

Reaction notes

Loading…