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

HRID 884508Notes

Reaction equation

HRID 884508 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-dihydro-4H-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-f074fb09caec46b685d2e8d234ad8e08
Source dataset
uspto-grants-2012_08
Patent number
US08242127B2

Reaction notes

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