2,4,6-Trimethylpyridine → HCID 18326535, compound

HRID 1250589Notes

Reaction equation

HRID 1250589 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].P(Cl)(Cl)(Cl)=O.N1C(C)=CC(C)=CC=1C.[ClH:30].[CH2:31]([O:34][CH2:35][CH2:36][NH2:37])[CH2:32][CH3:33].C(N(CC)CC)C>O>[Cl:30][C:9]1[N:8]=[C:7]([NH:37][CH2:36][CH2:35][O:34][CH2:31][CH2:32][CH3:33])[C:6]2[C:11](=[CH:12][CH:13]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[N:10]=1

Participants

7

Reactant 5

HCID 79532,4,6-TrimethylpyridineHCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 8169826-Nitro-2,4(1H,3H)-quinazolinedioneHCID 18326446221043-83-0

Product 1

HCID 18326535HCID 18326535, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 450 mg (2.17 mmol) of 6-nitroquinazoline-2,4(1H,3H)-dione were added 4.50 ml (48.28 mmol) of phosphorus oxychloride and 658 mg (5.43 mmol) of collidine, and the resulting mixture was subjected to heating under reflux for 24 hours. After phosphorus oxychloride was removed in vacuo, the mixture was dissolved in 10 ml of acetonitrile, followed by adding thereto 320 mg (2.29 mmol) of 2-propoxyethylamine hydrochloride and 3.51 ml (25.18 mmol) of triethylamine under ice cooling and stirring under ice cooling for 30 minutes. After water was added to the reaction solution, crystals thus precipitated were filtered to give 2-chloro-6-nitro-4-(2-propoxyethylamino)quinazoline. 5.00 ml (66.64 mmol) of allylamine was added to the compound, followed by stirring at room temperature for 5 hours. Water was added to the reaction solution, 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 346 mg (48.1%) of the title compound.

Workup

  1. temperatureto heating
  2. temperatureunder reflux for 24 hours
  3. customAfter phosphorus oxychloride was removed in vacuo
  4. dissolutionthe mixture was dissolved in 10 ml of acetonitrile
  5. additionby adding
  6. customthus precipitated
  7. filtrationwere filtered

Sources & evidence

ORD record
ord-a58ebcbc474f494e8407377b8a19604c
Source dataset
uspto-grants-2002_01
Patent number
US06339089B2

Reaction notes

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