2,4,6-Trimethylaniline → HCID 178486495, compound

HRID 2213708Notes

Reaction equation

HRID 2213708 reaction equation
Cl[C:2]1[CH:19]=[C:6]2[C:7]3[C:12]([CH2:13][CH2:14][N:5]2[C:4](=[O:20])[N:3]=1)=[CH:11][C:10]([O:15][CH3:16])=[C:9]([O:17][CH3:18])[CH:8]=3.[CH3:21][C:22]1[CH:28]=[C:27]([CH3:29])[CH:26]=[C:25]([CH3:30])[C:23]=1[NH2:24]>CC(O)C>[CH3:16][O:15][C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][C:9]=1[O:17][CH3:18])[C:6]1=[CH:19][C:2](=[N:24][C:23]3[C:25]([CH3:30])=[CH:26][C:27]([CH3:29])=[CH:28][C:22]=3[CH3:21])[NH:3][C:4](=[O:20])[N:5]1[CH2:14][CH2:13]2

Participants

4

Reactant 2

HCID 69132,4,6-TrimethylanilineHCID 46787202-Chloro-6,7-dihydro-9,10-dimethoxy-4H-pyrimido[6,1-a]isoquinolin-4-one

Product 1

HCID 178486495HCID 178486495, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

2-Chloro-9,10-dimethoxy-6,7-dihydro4H-pyrimido[6,1-a]isoquinolin-4-one, prepared according to Preparation 1, (38.5 g, 0.13 mol) and 2,4,6-trimethylaniline (52.7 g, 0.39 mol) in propan-2-ol (3 l) was stirred and heated at reflux, under nitrogen, for 24 h. After cooling to room temperature, the solution was evaporated in vacuo and the residue was purified by column chromatography on silica gel, eluting with CH2Cl2/MeOH, initially 98:2, changing to 96:4 once the product began to elute from the column. The title compound was obtained with a slight impurity, (just above the product on tlc). Yield 34.6 g, 67%.

Workup

  1. temperatureheated
  2. temperatureat reflux, under nitrogen, for 24 h
  3. customthe solution was evaporated in vacuo
  4. customthe residue was purified by column chromatography on silica gel
  5. washeluting with CH2Cl2/MeOH, initially 98:2
  6. washto elute from the column

Sources & evidence

ORD record
ord-89c1cb65b867461eb47f6d86b4c6f35b
Source dataset
uspto-grants-2006_09
Patent number
US07105663B2

Reaction notes

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