Cyclohexylamine → 4-Allylamino-2-cyclohexylamino-6-nitroquinazoline

HRID 1250560Notes

Reaction equation

HRID 1250560 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].[CH:19]1([NH2:25])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1>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:25][CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[N:6]=1)[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 7965CyclohexylamineHCID 183264874-Allylamino-2-chloro-6-nitroquinazoline

Product 1

HCID 183265254-Allylamino-2-cyclohexylamino-6-nitroquinazolineYield 76.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 250 mg (0.95 mmol) of 4-allylamino-2-chloro-6-nitroquinazoline and 867 mg (8.74 mmol) of cyclohexylamine was stirred at room temperature for 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 237 mg (yield: 76.6%) 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-e2fb1a51a3294b0eb33190164fa6f94a
Source dataset
uspto-grants-2002_01
Patent number
US06339089B2

Reaction notes

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