Allylamine → 2-Allylamino-6-nitro-4-pentylaminoquinazoline hydrochloride

HRID 1250577Notes

Reaction equation

HRID 1250577 reaction equation
[Cl:1][C:2]1[N:11]=[C:10]([NH:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([N+:18]([O-:20])=[O:19])[CH:8]=2)[N:3]=1.[CH2:21]([NH2:24])[CH:22]=[CH2:23]>O>[ClH:1].[CH2:21]([NH:24][C:2]1[N:11]=[C:10]([NH:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([N+:18]([O-:20])=[O:19])[CH:8]=2)[N:3]=1)[CH:22]=[CH2:23]

Participants

4

Reactant 2

HCID 7853AllylamineHCID 183263912-Chloro-6-nitro-4-pentylaminoquinazoline

Product 1

HCID 183264832-Allylamino-6-nitro-4-pentylaminoquinazoline hydrochloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 170 mg (0.61 mmol) of 2-chloro-6-nitro-4-pentylaminoquinazoline 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 160 mg (yield: 83.6%) of a free base compound 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-516397fc8f5b447485b202c2992de608
Source dataset
uspto-grants-2002_01
Patent number
US06339089B2

Reaction notes

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