Potassium Carbonate → 3-benzyl-7-chloro-2-[1-(2,2-dimethoxy-ethylamino)-2-methyl-propyl]-3H-quinazolin-4-one

HRID 490248Notes

Reaction equation

[NH2:1][CH:2]([C:6]1[N:15]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:14](=[O:23])[C:13]2[C:8](=[CH:9][C:10]([Cl:24])=[CH:11][CH:12]=2)[N:7]=1)[CH:3]([CH3:5])[CH3:4].[CH3:25][O:26][CH:27]([O:30][CH3:31])[CH2:28]Br.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:16]([N:15]1[C:14](=[O:23])[C:13]2[C:8](=[CH:9][C:10]([Cl:24])=[CH:11][CH:12]=2)[N:7]=[C:6]1[CH:2]([NH:1][CH2:28][CH:27]([O:30][CH3:31])[O:26][CH3:25])[CH:3]([CH3:5])[CH3:4])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

Conditions

Temperature: 135 °C

Procedure

To a solution of 2-(1-amino-2-methyl-propyl)-3-benzyl-7-chloro-3H-quinazolin-4-one (1.87 g, 5.48 mmol) in DMF (30 mL) was added bromoacetaldehyde dimethylacetal (2.78 g, 16.44 mmol) and potassium carbonate (2.27 g, 16.44 mmol) and the resulting suspension was heated at 135° C. for 18 h. The cooled reaction was concentrated in vacuo, triturated with methylene chloride to remove any solids, and the filtrate was concentrated in vacuo. The residue was purified by flash chromatography (silica gel; 2:1 hexanes:ethyl acetate) to give the title compound as a pale yellow oil (1.38 g, 59%). MS(ES+) m/e 430 [M+H]+.

Workup

customThe cooled reaction
concentrationwas concentrated in vacuo
customtriturated with methylene chloride
customto remove any solids
concentrationthe filtrate was concentrated in vacuo
customThe residue was purified by flash chromatography (silica gel; 2:1 hexanes:ethyl acetate)

Sources & evidence

ORD record: ord-f1e0313282cb4169a5e5d9438edf5719
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07528137B2

Reaction notes

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