Hydrochloric Acid → 2,4-Diallylamino-6-aminoquinazoline

HRID 1250566Notes

Reaction equation

HRID 1250566 reaction equation
O.O.[Sn](Cl)Cl.Cl.[CH2:7]([NH:10][C:11]1[N:20]=[C:19]([NH:21][CH2:22][CH:23]=[CH2:24])[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([N+:25]([O-])=O)[CH:17]=2)[N:12]=1)[CH:8]=[CH2:9].[OH-].[Na+]>>[CH2:7]([NH:10][C:11]1[N:20]=[C:19]([NH:21][CH2:22][CH:23]=[CH2:24])[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([NH2:25])[CH:17]=2)[N:12]=1)[CH:8]=[CH2:9]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 571174462,4-Diallylamino-6-nitroquinazoline

Product 1

HCID 207186892,4-Diallylamino-6-aminoquinazoline

Procedure

To 3.32 g (14.73 mmol) of tin (II) chloride dihydrate was added 14 ml of concentrated hydrochloric acid and 1.40 g (4.91 mmol) of 2,4-diallylamino-6-nitroquinazoline under ice cooling, and the resulting mixture was stirred at room temperature overnight. The reaction mixture was neutralized by adding an aqueous sodium hydroxide solution, followed by extraction with chloroform, 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 1.61 g (yield: 92.5%) of a free base compound of the title compound.

Workup

  1. extractionfollowed by extraction with chloroform
  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-1c114146388443129996fd05d61419bc
Source dataset
uspto-grants-2002_01
Patent number
US06339089B2

Reaction notes

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