Potassium Carbonate → 3-(3-But-2-enyl-5-isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl)-5-methyl-benzonitrile

HRID 2194759

Reaktionsgleichung

Reaktionsgleichung von HRID 2194759
[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-].[Li+].[CH2:31](Cl)[CH:32]=[CH:33][CH3:34]>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:32]=[CH:33][CH3:34]

Komponenten

6

Edukt 4

HCID 11430Potassium CarbonateHCID 11589Crotyl chlorideHCID 66321Lithium iodideHCID 468803773-(5-Isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl)-5-methyl-benzonitrile2×

Produkt 1

HCID 670504873-(3-But-2-enyl-5-isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl)-5-methyl-benzonitrileAusbeute 85,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a stirred solution of 3-(5-isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl)-5-methyl-benzonitrile (Compound 1) (297 mg, 1 mmol), anhydrous powdered potassium carbonate (165 mg, 1.2 mmol), and lithium iodide (134 mg, 1 mmol) in DMF (5 mL) at room temperature, was added crotyl chloride (97 μL, 1 mmol). After stirring for overnight, the mixture was evaporated in vacuo and the residue was purified by silica gel column chromatography (eluent, ethyl acetate:hexane (1:2)) to give 300 mg (85%) of 3-(3-but-2-enyl-5-isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl)-5-methyl-benzonitrile (80) as a white solid. The product was recrystallized from chloroform-ether-hexane to afford a white solid. m.p. 177-178° C.; 1H-NMR (300 MHz, CDCl3) δ 1.12 (3H, d, J=6.6 Hz), 1.21 (3H, d, J=6.6 Hz), 1.44 (3H, d, J=5.1 Hz), 2.22 (1H, m), 2.53 (3H, s), 4.02-4.20 (2H, m), 5.19-5.43 (2H, m), 7.78 (1H, s), 7.93 (1H, s), 8.03 (1H, s), 8.95 (1H, s). m/z (EI) 351 (M+).

Aufarbeitung

  1. customthe mixture was evaporated in vacuo
  2. customthe residue was purified by silica gel column chromatography (eluent, ethyl acetate:hexane (1:2))

Quellen und Nachweise

ORD-Eintrag
ord-f06452e5f7ea4b3684b924290a0e9bda
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08334295B2

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