2-Iodo-2-methylpropane → HCID 25214952, Verbindung

HRID 2194756

Reaktionsgleichung

[CH:1]([C:4]1[C:9](=[O:10])[NH:8][C:7](=[O:11])[NH:6][C:5]=1[C:12]([C:14]1[CH:15]=[C:16]([CH:19]=[C:20]([CH3:22])[CH:21]=1)[C:17]#[N:18])=[O:13])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].I[C:30]([CH3:33])([CH3:32])[CH3:31]>CN(C=O)C>[CH2:31]([N:6]1[C:5]([C:12]([C:14]2[CH:15]=[C:16]([CH:19]=[C:20]([CH3:22])[CH:21]=2)[C:17]#[N:18])=[O:13])=[C:4]([CH:1]([CH3:3])[CH3:2])[C:9](=[O:10])[NH:8][C:7]1=[O:11])[CH:30]([CH3:33])[CH3:32]

Komponenten

Reaktionsbedingungen

Temperatur: 55 °C

Versuchsvorschrift

To a stirred mixture of 3-(5-isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl)-5-methyl-benzonitrile (Compound 1) (1.19 g, 4 mmol) and powdered anhydrous potassium carbonate (662 mg, 4.8 mmol) in DMF (20 mL), was added 2-iodo-2-methylpropane (460 μL, 4 mmol). The mixture was then stirred in an oil bath (50-60° C.) for overnight and evaporated in vacuo. The residue was purified by silica gel column chromatography (eluent, ethyl acetate:hexane (1:2)) to afford 500 mg (35%) of 3-(3-isobutyl-5-isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl)-5-methyl-benzonitrile (78) as a white solid. m.p. 200-201° C.; 1H-NMR (200 MHz, CDCl3) δ 0.80 (3H, d, J=3.2 Hz), 0.83 (3H, d, J=3.2 Hz), 1.12 (3H, d, J=7.0 Hz), 1.23 (3H, d), J=7.0 Hz), 1.90 (1H, m), 2.25 (1H, m), 2.53 (3H, s), 2.93 (1H, dd, J=14.2 Hz, J=7.4 Hz), 3.75 (1H, dd, J=14.2 Hz, J=7.4 Hz), 7.80 (1H, s), 7.92 (1H, s), 8.03 (1H, s), 9.03 (1H, s); m/z (EI) 353 (M+).

Aufarbeitung

customevaporated in vacuo
customThe residue was purified by silica gel column chromatography (eluent, ethyl acetate:hexane (1:2))

Quellen und Nachweise

ORD-Eintrag: ord-40436ee506784885a00271e85cadea81
Quelldatensatz: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08334295B2

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