1,3-Dimethyl-2-imidazolidinone → 4-Butylamino-2-chloro-6-nitroquinazoline

HRID 1250574

Reaction equation

HRID 1250574 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=O)[NH:8][C:7]2=O)([O-:3])=[O:2].CN1CCN(C)C1=O.P(Cl)(Cl)([Cl:26])=O.[CH2:29]([NH2:33])[CH2:30][CH2:31][CH3:32]>O>[CH2:29]([NH:33][C:7]1[C:6]2[C:11](=[CH:12][CH:13]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[N:10]=[C:9]([Cl:26])[N:8]=1)[CH2:30][CH2:31][CH3:32]

Participants

6

Reactant 4

HCID 66611,3-Dimethyl-2-imidazolidinoneHCID 8007ButylamineHCID 24813Phosphorus oxychlorideHCID 8169826-Nitro-2,4(1H,3H)-quinazolinedione

Product 1

HCID 183264264-Butylamino-2-chloro-6-nitroquinazolineYield 63.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 500 mg (2.41 mmol) of 6-nitroquinazoline-2,4 (1H,3H)-dione were added 2 ml of 1,3-dimethyl-2-imidazolidinone and 8.23 g (53.64 mmol) of phosphorus oxychloride, and the resulting mixture was subjected to heating under reflux for 3 hours. After phosphorus oxychloride was removed in vacuo, the mixture was dissolved in 5 ml of acetonitrile, followed by addition of 5.9 ml (60 mmol) of butylamine and stirring under ice cooling for 30 minutes. To the reaction solution was added water, followed by extraction with ethyl acetate, washing with brine and drying over anhydrous sodium sulfate. After the solvent was distilled off, the residue was purified by a silica gel column to give 430 mg (yield: 63.6%) of the title compound.

Workup

  1. temperatureto heating
  2. temperatureunder reflux for 3 hours
  3. customAfter phosphorus oxychloride was removed in vacuo
  4. dissolutionthe mixture was dissolved in 5 ml of acetonitrile
  5. extractionfollowed by extraction with ethyl acetate
  6. washwashing with brine
  7. dry with materialdrying over anhydrous sodium sulfate
  8. distillationAfter the solvent was distilled off
  9. customthe residue was purified by a silica gel column

Sources & evidence

ORD record
ord-3143ca3b790840ec8a68b2398665282c
Source dataset
uspto-grants-2002_01
Patent number
US06339089B2

Linked notes

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