Diisopropylaniline → HCID 178486496, compound

HRID 884511Notes

Reaction equation

HRID 884511 reaction equation
[CH:1]([C:4]1[CH:10]=[CH:9][CH:8]=[C:7]([CH:11]([CH3:13])[CH3:12])[C:5]=1[NH2:6])([CH3:3])[CH3:2].Cl[C:15]1[CH:32]=[C:19]2[C:20]3[C:25]([CH2:26][CH2:27][N:18]2[C:17](=[O:33])[N:16]=1)=[CH:24][C:23]([O:28][CH3:29])=[C:22]([O:30][CH3:31])[CH:21]=3>CC(O)C>[CH:11]([C:7]1[CH:8]=[CH:9][CH:10]=[C:4]([CH:1]([CH3:3])[CH3:2])[C:5]=1[N:6]=[C:15]1[CH:32]=[C:19]2[C:20]3[C:25]([CH2:26][CH2:27][N:18]2[C:17](=[O:33])[NH:16]1)=[CH:24][C:23]([O:28][CH3:29])=[C:22]([O:30][CH3:31])[CH:21]=3)([CH3:13])[CH3:12]

Participants

4

Reactant 2

HCID 32484DiisopropylanilineHCID 46787202-Chloro-6,7-dihydro-9,10-dimethoxy-4H-pyrimido[6,1-a]isoquinolin-4-one

Product 1

HCID 178486496HCID 178486496, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

2,6-Diisopropylaniline (9.62 ml, 51 mmol) and 2-chloro-9,10-dimethoxy-6,7-dihydro-4H-pyrimido[6,1-a]isoquinolin-4-one (5 g, 17 mmol) were suspended in propan-2-ol (400 ml) and heated at reflux, under nitrogen, for 4 days. After cooling to room temperature, the solution was concentrated in vacuo and the residue purified by flash column chromatography [dichloromethane/methanol (98:2-96:4)] to afford the title compound (5.8 g, 79%) as a yellow/orange solid.

Workup

  1. temperatureheated
  2. temperatureat reflux, under nitrogen, for 4 days
  3. concentrationthe solution was concentrated in vacuo
  4. customthe residue purified by flash column chromatography [dichloromethane/methanol (98:2-96:4)]

Sources & evidence

ORD record
ord-5a25faea4a29434aa1e4a177c168e034
Source dataset
uspto-grants-2012_08
Patent number
US08242127B2

Reaction notes

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