N,N'-Dimethylethylenediamine → 3-(2-amino-6-quinazolinyl)-1-(3-chlorophenyl)-4-methyl-2(1H)-pyridinone

HRID 643516Notes

Reaction equation

[NH2:1][C:2]1[N:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:12]3[C:13](=[O:19])[NH:14][CH:15]=[CH:16][C:17]=3[CH3:18])[CH:8]=2)[N:3]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[Cl:28][C:29]1[CH:34]=[CH:33][CH:32]=[C:31](I)[CH:30]=1.CNCCNC>[Cu]I.O1CCOCC1>[NH2:1][C:2]1[N:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:12]3[C:13](=[O:19])[N:14]([C:31]4[CH:32]=[CH:33][CH:34]=[C:29]([Cl:28])[CH:30]=4)[CH:15]=[CH:16][C:17]=3[CH3:18])[CH:8]=2)[N:3]=1

Participants

Conditions

Temperature: 85 °C

Procedure

To a resealable tube was added a mixture of 3-(2-aminoquinazolin-6-yl)-4-methylpyridin-2(1H)-one (0.050 g, 0.20 mmol), potassium phosphate (0.084 g, 0.40 mmol), and copper(I) iodide (0.0075 g, 0.040 mmol) followed by Dioxane (2 mL), 1-chloro-3-iodobenzene (0.027 ml, 0.22 mmol) and N1,N2-dimethylethane-1,2-diamine (0.009 ml, 0.079 mmol). The resealable tube was purged with argon, sealed, and heated at 85° C. for 48 hrs. The crude mixture was filtered and concentrated in vacuo. The residue was purified by silica gel chromatography using 3-10% MeOH in CH2Cl2 with 1% NH4OH to afford 3-(2-amino-6-quinazolinyl)-1-(3-chlorophenyl)-4-methyl-2(1H)-pyridinone as an off-white solid. M+H+=363.1.

Workup

additionTo a resealable tube was added
customThe resealable tube was purged with argon
customsealed
filtrationThe crude mixture was filtered
concentrationconcentrated in vacuo
customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record: ord-0fbdaa8cf5454da79d399e800420538c
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07700607B2

Reaction notes

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