Water → 6,7-Dimethoxy-4-(1phenylcyclopropyl)-quinazoline

HRID 1871263

Reaction equation

[C:1]1([CH:7]2[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([N-]C(C)C)(C)C.[Li+].Cl[C:19]1[C:28]2[C:23](=[CH:24][C:25]([O:31][CH3:32])=[C:26]([O:29][CH3:30])[CH:27]=2)[N:22]=[CH:21][N:20]=1.O>O1CCCC1.C(OCC)(=O)C>[CH3:30][O:29][C:26]1[CH:27]=[C:28]2[C:23](=[CH:24][C:25]=1[O:31][CH3:32])[N:22]=[CH:21][N:20]=[C:19]2[C:7]1([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:9][CH2:8]1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 2.4 grams of phenylcyclopropane in 20 ml of tetrahydrofuran was added with 20 ml of 1M lithium diisopropylamide in tetrahydrofuran at 0° C. The mixture was stirred at 0° C. for 30 minutes and room temperature for 20 minutes. This was then added with 3.0 grams of 4-chloro-6,7-dimethoxyquinazoline in 20 ml of tetrahydrofuran. The mixture was then stirred at room temperature overnight, poured into a mixture of cold water and ethyl acetate. The ethyl acetate layer was washed with brine, dried over sodium sulfate, filtered and concentrated. The crude was then purified on a silica gel column with dichloromethane and methanol as the solvent to provided 550 mg of 6,7-dimethoxy-4-(1phenylcyclopropyl)-quinazoline.

Workup

stirringThe mixture was then stirred at room temperature overnight
washThe ethyl acetate layer was washed with brine
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated
customThe crude was then purified on a silica gel column with dichloromethane and methanol as the solvent

Sources & evidence

ORD record: ord-6b79703d080846739088e9b0b87de7d7
Source dataset: uspto-grants-2000_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06103728

Linked notes

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