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Dimethylformamide → 4H-Pyrimido(6,1-a)isoquinolin-4-one, 2,3,6,7-tetrahydro-9,10-dimethoxy-3-(1-methylethyl)-2-((2,4,6-trimethylphenyl)imino)-

HRID 745310
Notes
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Reaction equation

HRID 745310 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][CH2:6]2.CN(C)C=O.[H-].[Na+].[CH:37](I)([CH3:39])[CH3:38]>CO>[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]([CH:37]([CH3:39])[CH3:38])[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][CH2:6]2.[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]([CH:37]([CH3:39])[CH3:38])[C:18](=[O:19])[N:8]1[CH2:7][CH2:6]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6362Isopropyl iodideHCID 24758Sodium hydrideHCID 18694579,10-dimethoxy-2-(2,4,6-trimethylanilino)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one

Product 2

HCID 30619524H-Pyrimido(6,1-a)isoquinolin-4-one, 2,3,6,7-tetrahydro-9,10-dimethoxy-3-(1-methylethyl)-2-((2,4,6-trimethylphenyl)imino)-
HCID 3068154
4H-Pyrimido(6,1-a)isoquinolin-4-one, 6,7-dihydro-9,10-dimethoxy-2-((1-methylethyl)(2,4,6-trimethylphenyl)amino)-

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

9,10-Dimethoxy-2-(2,4,6-trimethylanilino)-6,7-dihydro-4H-pyrimido(6,1-a)isoquinolin-4-one (5.85 g) and dimethylformamide (30 ml) are added to oil-free sodium hydride (1.5 g). The mixture is heated for 5 minutes to 110° C. and then cooled to room temperature. Isopropyl iodide (2.55 g) is added and the whole is heated to 110° C. for 40 hours. After cooling, methanol is added to the reaction mixture and the solvents are removed under reduced pressure. The residue is extracted with chloroform, the extract washed with water, dried over sodium sulfate and evaporated to dryness. The residue is chromatographed to give the bases (a) m.p. 182°-183° C. and (b) m.p. 178°-179° C.

Workup

  1. temperatureThe mixture is heated for 5 minutes to 110° C.
  2. temperaturethe whole is heated to 110° C. for 40 hours
  3. temperatureAfter cooling
  4. customthe solvents are removed under reduced pressure
  5. extractionThe residue is extracted with chloroform
  6. washthe extract washed with water
  7. dry with materialdried over sodium sulfate
  8. customevaporated to dryness
  9. customThe residue is chromatographed

Sources & evidence

ORD record
ord-171aabe56e344b2a95a6b221a6749a06
Source dataset
uspto-grants-1986_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04598148

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes