Methyl iodide → HCID 3065644, compound

HRID 1380226Notes

Reaction equation

HRID 1380226 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]([NH:20][C:21]3[C:26]([CH3:27])=[CH:25][C:24]([CH3:28])=[CH:23][C:22]=3[CH3:29])=[N:17][C:18](=[O:19])[N:8]1[CH2:7][CH:6]2[CH3:30].CI.[C:33](=O)([O-])[O-].[K+].[K+]>CC(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](=[N:20][C:21]3[C:26]([CH3:27])=[CH:25][C:24]([CH3:28])=[CH:23][C:22]=3[CH3:29])[N:17]([CH3:33])[C:18](=[O:19])[N:8]1[CH2:7][CH:6]2[CH3:30]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 3065550HCID 3065550, compound

Product 1

HCID 3065644HCID 3065644, compoundYield 50.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

18 g of 6,7-dihydro-9,10-dimethoxy-2-mesitylamino-7-methyl-4H-pyrimido[6,1-a]isoquinolin-4-one are boiled under reflux in 1.5 l of acetone with 270 ml of methyl iodide in the presence of 90 g of potassium carbonate. The mixture is then filtered and the filtrate is evaporated. The residue is dissolved in chloroform and purified by chromatography on a silica gel column. There are obtained 9.4 g of pure 9,10-dimethoxy-3,7-dimethyl-2-mesitylimino-2,3,6,7-tetrahydro-4H-pyrimido[6,1-a]isoquinolin-4-one, m.p. 156°-157° C. The corresponding hydrochloride of the compound melts at 224° C. (decomposition).

Workup

  1. filtrationThe mixture is then filtered
  2. customthe filtrate is evaporated
  3. dissolutionThe residue is dissolved in chloroform
  4. custompurified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-522fd7d301914c10aa9ce25613816732
Source dataset
uspto-grants-1986_04
Patent number
US04581172

Reaction notes

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