Diethylamine → HCID 135858485, compound

HRID 1616120Notes

Reaction equation

Cl[CH2:2][C:3]1[NH:12][C:11](=[O:13])[C:10]2[C:5](=[CH:6][C:7]([C:14]([O:16][CH3:17])=[O:15])=[CH:8][CH:9]=2)[N:4]=1.[CH2:18]([N:20](CC)[CH2:21][CH3:22])[CH3:19].C(NCC)C>CN(C=O)C>[CH2:18]([N:20]([CH2:2][C:3]1[NH:12][C:11](=[O:13])[C:10]2[C:5](=[CH:6][C:7]([C:14]([O:16][CH3:17])=[O:15])=[CH:8][CH:9]=2)[N:4]=1)[CH2:21][CH3:22])[CH3:19]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of methyl 2-(chloromethyl)-4-oxo-3,4-dihydroquinazoline-7-carboxylate (160 mg, 0.63 mmol) in DMF (3 mL) was added triethylamine (0.176 mL, 1.27 mmol) and diethylamine (0.33 mL, 3.17 mmol). The reaction mixture was heated to 100° C. and stirred for 3 h. The mixture was then cooled to rt and concentrated. The residue was purified by flash silica gel chromatography (0% to 10% MeOH/DCM) to afford methyl 2-[(diethylamino)methyl]-4-oxo-3,4-dihydroquinazoline-7-carboxylate (0.15 g, 81%). LC-MS: (FA) ES+ 290.

Workup

temperatureThe mixture was then cooled to rt
concentrationconcentrated
customThe residue was purified by flash silica gel chromatography (0% to 10% MeOH/DCM)

Sources & evidence

ORD record: ord-63c6ca0dd5b647a6980bbf271a908167
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765773B2

Reaction notes

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