2-Methoxyethylamine → 4-Allylamino-2-(2-methoxyethylamino)-6-nitroquinazoline

HRID 1250561Notes

Reaction equation

HRID 1250561 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].[CH3:19][O:20][CH2:21][CH2:22][NH2:23]>O>[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:23][CH2:22][CH2:21][O:20][CH3:19])[N:6]=1)[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 80182-MethoxyethylamineHCID 183264874-Allylamino-2-chloro-6-nitroquinazoline

Product 1

HCID 183264144-Allylamino-2-(2-methoxyethylamino)-6-nitroquinazolineYield 74.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 250 mg (0.95 mmol) of 4-allylamino-2-chloro-6-nitroquinazoline and 864 mg (11.50 mmol) of 2-methoxyethylamine was stirred at room temperature for 2.5 hours. Water was added to the reaction mixture, 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 214 mg (yield: 74.7%) 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-39c07896df9247f4b01a1638c2940320
Source dataset
uspto-grants-2002_01
Patent number
US06339089B2

Reaction notes

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