Triethylamine → 4-(2-Aminobenzylamino)-7-ethylamino-6-nitroquinazoline

HRID 365761Notes

Reaction equation

HRID 365761 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([NH:15][CH2:16][CH3:17])=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.C(N(CC)CC)C.[NH2:25][C:26]1[CH:33]=[CH:32][CH:31]=[CH:30][C:27]=1[CH2:28][NH2:29]>O1CCCC1>[NH2:25][C:26]1[CH:33]=[CH:32][CH:31]=[CH:30][C:27]=1[CH2:28][NH:29][C:2]1[C:11]2[C:6](=[CH:7][C:8]([NH:15][CH2:16][CH3:17])=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1780962-(Aminomethyl)anilineHCID 232929894-Chloro-7-ethylamino-6-nitroquinazoline

Product 1

HCID 232930134-(2-Aminobenzylamino)-7-ethylamino-6-nitroquinazolineYield 78.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Chloro-7-ethylamino-6-nitroquinazoline (5.00 g, 19.8 mmol), triethylamine (8.3 ml, 60.9 mmol), and 2-aminobenzylamine (2.9 g, 23.8 mmol) were stirred at room temperature overnight in tetrahydrofuran. After the reaction was completed, the solution was concentrated under reduced pressure, and the resulting solids were washed with methanol to give the title compound (5.23 g, 78%).

Workup

  1. concentrationthe solution was concentrated under reduced pressure
  2. washthe resulting solids were washed with methanol

Sources & evidence

ORD record
ord-faac0658e24944a9adef8d8190e97f56
Source dataset
uspto-grants-2000_10
Patent number
US06127541

Reaction notes

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