Lithium Chloride → 4-(Methylthio)-6-methoxy-7-(3-hydroxyprop-1-enyl)quinazoline

HRID 2233263Notes

Reaction equation

[CH3:1][S:2][C:3]1[C:12]2[C:7](=[CH:8][C:9](OS(C(F)(F)F)(=O)=O)=[C:10]([O:13][CH3:14])[CH:11]=2)[N:6]=[CH:5][N:4]=1.C([Sn](CCCC)(CCCC)/[CH:28]=[CH:29]/[CH2:30][OH:31])CCC.[Cl-].[Li+]>CN(C)C=O>[CH3:1][S:2][C:3]1[C:12]2[C:7](=[CH:8][C:9]([CH:28]=[CH:29][CH2:30][OH:31])=[C:10]([O:13][CH3:14])[CH:11]=2)[N:6]=[CH:5][N:4]=1

Participants

Conditions

Temperature: 65 °C

Procedure

A suspension of 4-(methylthio)-6-methoxy-7-(trifluoromethanesulphonyloxy)quinazoline (1.1 g, 3.1 mmol), E-3-(tributylstannyl)-2-propen-1-ol (1.12 g, 3.23 mmol), bisdichloro(triphenylphosphine)palladium (44 mg, 0.06 mmol) and lithium chloride (395 mg, 9.32 mmol) in dimethylformamide (14 ml) was heated at 65° C. for 3 hours. The mixture was cooled to ambient temperature, the solid was recovered by suction filtration and washed with ether. Drying in vacuo yielded 4-(methylthio)-6-methoxy-7-(3-hydroxyprop-1-enyl)quinazoline (355 mg, 44% yield):

Workup

temperatureThe mixture was cooled to ambient temperature
filtrationthe solid was recovered by suction filtration
washwashed with ether
customDrying in vacuo

Sources & evidence

ORD record: ord-f8b38680b5e1423a8e403496dec44a50
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07709479B1

Reaction notes

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