2-Chloro-6,7-dimethoxy-4-quinazolinamine → HCID 20306021, compound

HRID 1732331Notes

Reaction equation

HRID 1732331 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[C:4]([Cl:16])[N:3]=1.[O:17]([CH2:24][CH:25]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[O:26][CH:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(O)CCC>[OH2:12].[ClH:16].[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[C:4]([N:30]2[CH2:29][CH2:28][CH:27]([O:26][CH:25]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[CH2:24][O:17][C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH2:32][CH2:31]2)[N:3]=1

Participants

4

Reactant 2

HCID 902352-Chloro-6,7-dimethoxy-4-quinazolinamineHCID 20306017HCID 20306017, compound

Product 1

HCID 20306021HCID 20306021, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

4-Amino-2-chloro-6,7-dimethoxyquinazoline (1.44 g.) and 4-(2-phenoxy-1-phenylethoxy)piperidine (2.0 g.) in n-butanol (100 ml.) were heated under reflux for 20 hours. The solvent was then evaporated in vacuo, the residue triturated with ether and crystallized from isopropanol. The solid was partitioned between chloroform and aqueous sodium carbonate solution, the chloroform extract dried (MgSO4) and the solvent evaporated in vacuo. The residue was chromatographed on silica (100 g.) eluting with chloroform followed by chloroform methanol (20:1). Fractions containing the product were combined, the solvent evaporated in vacuo and the residue converted to the hydrochloride salt by treatment of a chloroform solution with ethereal hydrogen chloride.

Workup

  1. temperatureunder reflux for 20 hours
  2. customThe solvent was then evaporated in vacuo
  3. customthe residue triturated with ether
  4. customcrystallized from isopropanol
  5. customThe solid was partitioned between chloroform and aqueous sodium carbonate solution
  6. extractionthe chloroform extract
  7. dry with materialdried (MgSO4)
  8. customthe solvent evaporated in vacuo
  9. customThe residue was chromatographed on silica (100 g.)
  10. washeluting with chloroform
  11. additionFractions containing the product
  12. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-50f6d3ddb6d24e8c9f871d79834357b8
Source dataset
uspto-grants-1980_12
Patent number
US04237138

Reaction notes

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