Methyl iodide → 1-(4-Methoxy-benzyl)-4-methyl-4-phenyl-3,4-dihydro-1H-quinazolin-2-one

HRID 1497735Notes

Reaction equation

[CH3:1][C:2]1([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][C:4](=[O:12])[NH:3]1.Cl[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1.C([O-])([O-])=O.[Cs+].[Cs+].CI>CN(C=O)C.O>[CH3:28][O:27][C:24]1[CH:25]=[CH:26][C:21]([CH2:20][N:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:2]([CH3:1])([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[NH:3][C:4]2=[O:12])=[CH:22][CH:23]=1

Participants

Conditions

Temperature: -20 °C

Procedure

To a solution of 4-Methyl-4-phenyl-3,4-dihydro-1H-quinazolin-2-one (0.70 g, 2.9 mmol) in DMF (10 mL) is added 1-chloromethyl-4-methoxy-benzene and Cs2CO3 (1.92 g, 5.9 mmol). After the addition the mixture is stirred at −20° C. for 1 h. Then CH3I (2.6 g, 18 mmol) is added dropwise. After the addition the mixture is heated to refluxed overnight. H2O is then added and the mixture extracted with EtOAc which is dried over Na2SO4 and concentrated. The residue is purified by chromatography on silica gel to give product.

Workup

additionAfter the addition the mixture
additionAfter the addition the mixture
temperatureis heated
temperatureto refluxed overnight
extractionthe mixture extracted with EtOAc which
dry with materialis dried over Na2SO4
concentrationconcentrated
customThe residue is purified by chromatography on silica gel
customto give product

Sources & evidence

ORD record: ord-6c60a7ff844940e3b95f988f98bd70fa
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09199988B2

Reaction notes

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