Phosphorus tribromide → 2-(2-Bromoethyl)-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinazoline

HRID 266122Notes

Reaction equation

P(Br)(Br)[Br:2].[CH3:5][O:6][C:7]1[CH:8]=[C:9]([C:15]2[C:24]3[C:19](=[CH:20][C:21]([O:27][CH3:28])=[C:22]([O:25][CH3:26])[CH:23]=3)[N:18]=[C:17]([CH2:29][CH2:30]O)[N:16]=2)[CH:10]=[CH:11][C:12]=1[O:13][CH3:14].C(=O)(O)[O-].[Na+]>C1C=CC=CC=1>[Br:2][CH2:30][CH2:29][C:17]1[N:16]=[C:15]([C:9]2[CH:10]=[CH:11][C:12]([O:13][CH3:14])=[C:7]([O:6][CH3:5])[CH:8]=2)[C:24]2[C:19](=[CH:20][C:21]([O:27][CH3:28])=[C:22]([O:25][CH3:26])[CH:23]=2)[N:18]=1

Participants

Conditions

Temperature: 75 °C

Procedure

Phosphorus tribromide (PBr3)(0.95 g) was added dropwise to a solution of 4-(3,4-dimethoxyphenyl)-2-(2-hydroxyethyl)-6,7-dimethoxyquinazoline (2.6 g) in benzene (50 ml) at room temperature. The mixture was stirred at 75° C. for 1 hour, poured into ice-cold water, neutralized with an aqueous saturated solution of sodium bicarbonate, and then extracted with chloroform. The chloroform layer was washed with water, dried over magnesium sulfate, and the solvent was evaporated. The residue was subjected to column chromatography on silica gel. The fractions eluted with chloroform-ethyl acetate (3:1, v/v) gave 2-(2-bromoethyl)-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinazoline (1.1 g, 37%). This was recrystallized from ethyl acetate. Colorless needles, mp. 166°-167° C.

Workup

additionpoured into ice-cold water
extractionextracted with chloroform
washThe chloroform layer was washed with water
dry with materialdried over magnesium sulfate
customthe solvent was evaporated
washThe fractions eluted with chloroform-ethyl acetate (3:1

Sources & evidence

ORD record: ord-37045bb94f43476c897b4c3d1d45681e
Source dataset: uspto-grants-1997_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05650410

Reaction notes

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