Allylamine → 2-Allylamino-4-butylamino-6-nitroquinazoline

HRID 1250575Notes

Reaction equation

HRID 1250575 reaction equation
[CH2:1]([NH:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([N+:16]([O-:18])=[O:17])[CH:14]=2)[N:9]=[C:8](Cl)[N:7]=1)[CH2:2][CH2:3][CH3:4].[CH2:20]([NH2:23])[CH:21]=[CH2:22]>O>[CH2:20]([NH:23][C:8]1[N:7]=[C:6]([NH:5][CH2:1][CH2:2][CH2:3][CH3:4])[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([N+:16]([O-:18])=[O:17])[CH:14]=2)[N:9]=1)[CH:21]=[CH2:22]

Participants

4

Reactant 2

HCID 7853AllylamineHCID 183264264-Butylamino-2-chloro-6-nitroquinazoline

Product 1

HCID 183264552-Allylamino-4-butylamino-6-nitroquinazolineYield 82.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 170 mg (0.67 mmol) of 4-butylamino-2-chloro-6-nitroquinazoline was added 1.52 g (26.66 mmol) of allylamine, followed by stirring at room temperature overnight. To the reaction solution was water added, 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 166 mg (yield: 82.1%) of the title compound.

Workup

  1. additionadded
  2. extractionfollowed by extraction with ethyl acetate
  3. washwashing with brine
  4. dry with materialdrying over anhydrous sodium sulfate
  5. distillationAfter the solvent was distilled off
  6. customthe residue was purified by a silica gel column

Sources & evidence

ORD record
ord-4c92adf3a733449299ce3d691aa61ce5
Source dataset
uspto-grants-2002_01
Patent number
US06339089B2

Reaction notes

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