Triethylamine → 4-Allylamino-2-(3-methyl-2-butenylamino)-6-nitroquinazoline

HRID 1250609Notes

Reaction equation

HRID 1250609 reaction equation
[CH2:1]([NH:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([N+:15]([O-:17])=[O:16])[CH:13]=2)[N:8]=[C:7](Cl)[N:6]=1)[CH:2]=[CH2:3].Cl.[CH3:20][C:21]([CH3:25])=[CH:22][CH2:23][NH2:24].C(N(CC)CC)C>C(#N)C>[CH2:1]([NH:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([N+:15]([O-:17])=[O:16])[CH:13]=2)[N:8]=[C:7]([NH:24][CH2:23][CH:22]=[C:21]([CH3:25])[CH3:20])[N:6]=1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 183264874-Allylamino-2-chloro-6-nitroquinazolineHCID 183265643-Methylbut-2-en-1-amine hydrochloride

Product 1

HCID 183264584-Allylamino-2-(3-methyl-2-butenylamino)-6-nitroquinazolineYield 75.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 10 ml of a solution of 150 mg (0.57 mmol) of 4-allylamino-2-chloro-6-nitroquinazoline in acetonitrile were added 137 mg (1.13 mmol) of 3-methyl-2-butenylamine hydrochloride and 288 mg (2.85 mmol) of triethylamine, followed by heating at room temperature for 4.5 hours. After completion of the reaction, ice water was added to the reaction mixture, followed by extraction with chloroform (10 ml×3). After the organic layer was washed with brine and then dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The residue was purified by a silica gel chromatography to give 133 mg (yield: 75.1%) of the title compound.

Workup

  1. additionwas added to the reaction mixture
  2. extractionfollowed by extraction with chloroform (10 ml×3)
  3. washAfter the organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by a silica gel chromatography

Sources & evidence

ORD record
ord-0ae06b1a4e6d48ff9a460583c79f13eb
Source dataset
uspto-grants-2002_01
Patent number
US06339089B2

Reaction notes

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