1,3-Dimethyl-2-imidazolidinone → HCID 178455440, compound

HRID 2069190Notes

Reaction equation

F[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])[NH:8][C:7](=[O:15])[N:6]([NH:16][S:17]([CH3:20])(=[O:19])=[O:18])[C:5]2=[O:21].[C:22]([SiH2:26][O:27][C:28]([CH3:35])([CH3:34])[C:29]1[N:30]=[CH:31][NH:32][CH:33]=1)([CH3:25])([CH3:24])[CH3:23].CN1CCN(C)C1=O>C(OCC)(=O)C>[C:22]([SiH2:26][O:27][C:28]([CH3:35])([CH3:34])[C:29]1[N:30]=[CH:31][N:32]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][C:11]=2[N+:12]([O-:14])=[O:13])[NH:8][C:7](=[O:15])[N:6]([NH:16][S:17]([CH3:20])(=[O:19])=[O:18])[C:5]3=[O:21])[CH:33]=1)([CH3:25])([CH3:23])[CH3:24]

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of 100 mg (0.314 mmol) of N-(6-fluoro-7-nitro-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl)-methanesulfonamide, 333 mg (1.57 mmol) of 4-(tert-butyl-dimethyl-silanyloxymethyl)-1H-imidazole and 1 ml of dry 1,3-dimethyl-2-imidazolidinone is heated to 140° C. (oil bath temperature) in a closed vial for 4 hours. After cooling, the orange solution is diluted with ethyl acetate and the organic phase washed with water and brine and dried over Na2SO4. Evaporation of the solvent gives an oil which is purified by medium pressure chromatography on silica gel with ethyl acetate/acetic acid 98:2 as eluent, yielding 53 mg of N-{6-[4-(tert-butyl-dimethyl-silanyloxymethyl)-imidazol-1-yl]-7-nitro-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl}-methanesulfonamide, m.p. >270° C.

Workup

temperatureAfter cooling
washthe organic phase washed with water and brine
dry with materialdried over Na2SO4
customEvaporation of the solvent
customgives an oil which
customis purified by medium pressure chromatography on silica gel with ethyl acetate/acetic acid 98:2 as eluent

Sources & evidence

ORD record: ord-46c8499e1b174c4cb897282dc14cd3e1
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08299085B2

Reaction notes

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