Thiomorpholine → 7-Ethylamino-6-nitro-4-(5-thiomorpholinopentylamino)quinazoline

HRID 2258433Notes

Reaction equation

HRID 2258433 reaction equation
[NH:1]1[CH2:6][CH2:5][S:4][CH2:3][CH2:2]1.Cl[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:14]1[C:23]2[C:18](=[CH:19][C:20]([NH:27][CH2:28][CH3:29])=[C:21]([N+:24]([O-:26])=[O:25])[CH:22]=2)[N:17]=[CH:16][N:15]=1>CN(C)C=O>[CH2:28]([NH:27][C:20]1[CH:19]=[C:18]2[C:23]([C:14]([NH:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][N:1]3[CH2:6][CH2:5][S:4][CH2:3][CH2:2]3)=[N:15][CH:16]=[N:17]2)=[CH:22][C:21]=1[N+:24]([O-:26])=[O:25])[CH3:29]

Participants

4

Reactant 2

HCID 67164ThiomorpholineHCID 229218864-(5-Chloropentylamino)-7-ethylamino-6-nitroquinazoline

Product 1

HCID 229218157-Ethylamino-6-nitro-4-(5-thiomorpholinopentylamino)quinazolineYield 98.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Thiomorpholine (6 ml, 59.7 mmol) was added to a dimethylformamide solution (30 ml) of 4-(5-chloropentylamino)-7-ethylamino-6-nitroquinazoline (2.50 g, 7.41 mmol) obtained in Reference Example 66 and the mixture was heated under reflux for 3 hours. After the solvent was distilled off, the residue was purified by silica gel column chromatography (chloroform:methanol=30:1) to give the title compound (2.95 g, 98.7%).

Workup

  1. customobtained in Reference Example 66
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 3 hours
  4. distillationAfter the solvent was distilled off
  5. customthe residue was purified by silica gel column chromatography (chloroform:methanol=30:1)

Sources & evidence

ORD record
ord-b4e4816a8fa14816b80fb331f101738d
Source dataset
uspto-grants-1997_08
Patent number
US05661147

Reaction notes

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