Triethylamine → HCID 9927305, compound

HRID 1106512Notes

Reaction equation

HRID 1106512 reaction equation
Cl[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]=[CH:4][N:3]=1.[C:16]1([C@@H:22]([CH2:24][OH:25])[NH2:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(N(CC)CC)C>C(O)(C)C>[OH:25][CH2:24][C@@H:22]([NH:23][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]=[CH:4][N:3]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1347972-Amino-2-phenylethan-1-olHCID 27693644-Chloro-6,7-dimethoxyquinazoline

Product 1

HCID 9927305HCID 9927305, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 4-chloro-6,7-dimethoxyquinazoline (225 mg, 1 mmol), (S)-2-phenylglycinol (137.2 mg, 1 mmol) and triethylamine (304 mg, 3 mmol) in isopropanol (7 ml) was heated to reflux for about 8 h. Then the mixture was evaporated under vacuum to dryness and the residue purified by gradient elution chromatography on silica gel using as eluant dichloromethane/ethanol 2-6%. Thus pure title compound was obtained in 70% yield (228 mg).

Workup

  1. temperatureto reflux for about 8 h
  2. customThen the mixture was evaporated under vacuum to dryness
  3. customthe residue purified by gradient elution chromatography on silica gel using as eluant dichloromethane/ethanol 2-6%

Sources & evidence

ORD record
ord-95b5854109cc47f1865f4033460ccf6c
Source dataset
uspto-grants-2000_05
Patent number
US06057326

Reaction notes

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