Allylamine → 2-Allylamino-4-isopropylamino-6-nitroquinazoline hydrochloride

HRID 1250583

Reaction equation

HRID 1250583 reaction equation
[Cl:1][C:2]1[N:11]=[C:10]([NH:12][CH:13]([CH3:15])[CH3:14])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([N+:16]([O-:18])=[O:17])[CH:8]=2)[N:3]=1.[CH2:19]([NH2:22])[CH:20]=[CH2:21]>O>[ClH:1].[CH2:19]([NH:22][C:2]1[N:11]=[C:10]([NH:12][CH:13]([CH3:15])[CH3:14])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([N+:16]([O-:18])=[O:17])[CH:8]=2)[N:3]=1)[CH:20]=[CH2:21]

Participants

4

Reactant 2

HCID 7853AllylamineHCID 183264282-Chloro-4-isopropylamino-6-nitroquinazoline

Product 1

HCID 183265012-Allylamino-4-isopropylamino-6-nitroquinazoline hydrochloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 870 mg (3.26 mmol) of 2-chloro-4-isopropylamino-6-nitroquinazoline was added 3.81 g (66.64 mmol) of allylamine, followed by stirring at room temperature for 4 hours. 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 895 mg (yield: 95.7%) of a free base compound of the title compound.

Workup

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

Sources & evidence

ORD record
ord-3452785b83ad483896bc3e4eef052c71
Source dataset
uspto-grants-2002_01
Patent number
US06339089B2

Linked notes

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