Methyl iodide → HCID 12788091, compound

HRID 1979718Notes

Reaction equation

HRID 1979718 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[C:9]1=[CH:15][C:16](=[O:20])[NH:17][C:18](=[O:19])[N:8]1[CH2:7][CH2:6]2.[H-].[Na+].[CH3:23]I>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[C:9]1=[CH:15][C:16](=[O:20])[N:17]([CH3:23])[C:18](=[O:19])[N:8]1[CH2:7][CH2:6]2

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 908572HCID 908572, compound

Product 1

HCID 12788091HCID 12788091, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 9,10-dimethoxy-3,4,6,7-tetrahydro-2H-pyrimido(6,1-a)isoquinolin-2,4-dione (4.11 g), oil-free sodium hydride (0.75 g) and dimethylformamide (100 ml) is heated for 15 minutes to 100° C. and then cooled to room temperature. Methyl iodide (10 ml) is added and the reaction mixture is heated for 12 hours to 100° C. The solvent is removed under reduced pressure and the residue treated with cold water. The solid matter is filtered off and recrystallized from ethyl acetate/methylene chloride. Yield 4.0 g, melting point 260°-262° C.

Workup

  1. temperatureis heated for 15 minutes to 100° C.
  2. temperaturethe reaction mixture is heated for 12 hours to 100° C
  3. customThe solvent is removed under reduced pressure
  4. additionthe residue treated with cold water
  5. filtrationThe solid matter is filtered off
  6. customrecrystallized from ethyl acetate/methylene chloride

Sources & evidence

ORD record
ord-8c47efbc879b4cdd89fc3a9676684df5
Source dataset
uspto-grants-1984_11
Patent number
US04482556

Reaction notes

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