Methyl iodide → HCID 20097000, compound

HRID 1769597Notes

Reaction equation

HRID 1769597 reaction equation
[OH:1][C:2]1[C:3]2[C:4](=[N:8][O:9][N+:10]=2[O-:11])[N:5]=[CH:6][N:7]=1.[H-].[Li+].[CH3:14]I>C1COCC1.C(OCC)(=O)C>[CH3:14][N:7]1[C:2](=[O:1])[C:3]2=[N+:10]([O-:11])[O:9][N:8]=[C:4]2[N:5]=[CH:6]1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 62714Lithium hydrideHCID 178526302HCID 178526302, compound

Product 1

HCID 20097000HCID 20097000, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

A solution of 3.0 g (20 mmol) of 7-hydroxy-[1,2,5]oxadiazolo[3,4-d]pyrimidine-1-oxide (C. Temple, C. L. Kussner, J. A. Montgomery, J. Org. Chem. 33 (1968) 2086) in 30 ml of THF is added dropwise to a suspension of 0.18 g (22.5 mmol) of lithium hydride in 20 ml of THF. The mixture is heated at 40° C. for 30 minutes, then 11.5 g (80 mmol) of methyl iodide in 10 ml of THF are added dropwise at room temperature and it is allowed to stand for 2 days. The mixture is diluted with 300 ml of ethyl acetate, washed three times with water, dried over magnesium sulphate and concentrated in vacuo. After recrystallisation from isopropanol, 1.9 g (57%) of 6-methyl-[1,2,5]oxadiazolo[3,4-d]pyrimidine-7(6H)-one-1-oxide are obtained.

Workup

  1. washwashed three times with water
  2. dry with materialdried over magnesium sulphate
  3. concentrationconcentrated in vacuo
  4. customAfter recrystallisation from isopropanol, 1.9 g (57%) of 6-methyl-[1,2,5]oxadiazolo[3,4-d]pyrimidine-7(6H)-one-1-oxide
  5. customare obtained

Sources & evidence

ORD record
ord-29a38979fb2947c58a92c234b27feb30
Source dataset
uspto-grants-1995_01
Patent number
US05382585

Reaction notes

Loading…