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Acetamidine monohydrochloride → 2'-Methoxy-4'-[(2-methyl-6-oxo-4-propyl-1,6-dihydropyrimidin-5-yl)methyl]biphenyl-2-carbonitrile

HRID 1674252
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1674252
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH:16]([C:22](=O)[CH2:23][CH2:24][CH3:25])[C:17](OCC)=[O:18])=[CH:11][C:10]=1[O:27][CH3:28])#[N:2].Cl.[C:30](=[NH:33])([NH2:32])[CH3:31].C[O-].[Na+]>CO>[CH3:28][O:27][C:10]1[CH:11]=[C:12]([CH2:15][C:16]2[C:17](=[O:18])[NH:32][C:30]([CH3:31])=[N:33][C:22]=2[CH2:23][CH2:24][CH3:25])[CH:13]=[CH:14][C:9]=1[C:4]1[C:3]([C:1]#[N:2])=[CH:8][CH:7]=[CH:6][CH:5]=1
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Komponenten

5

Edukt 3

HCID 67170Acetamidine monohydrochlorideHCID 10942334Sodium MethoxideHCID 57460898Ethyl 2-[(2'-cyano-2-methoxybiphenyl-4-yl)methyl]-3-oxohexanoate

Produkt 1

HCID 1361468682'-Methoxy-4'-[(2-methyl-6-oxo-4-propyl-1,6-dihydropyrimidin-5-yl)methyl]biphenyl-2-carbonitrileAusbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887
Methanol
Lösungsmittel

Versuchsvorschrift

To a suspension of 60% sodium hydride (1.80 g) in tetrahydrofuran (50 mL) was added dropwise a solution of ethyl butyrylacetate (9.50 g) in tetrahydrofuran (30 mL). After stirring for 30 min, 4′-(bromomethyl)-2′-methoxybiphenyl-2-carbonitrile (8.79 g) was added. The mixture was stirred at room temperature for 15 hr, and 1 M hydrochloric acid was added. The mixture was extracted with ethyl acetate, and the organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography to give ethyl 2-[(2′-cyano-2-methoxybiphenyl-4-yl)methyl]-3-oxohexanoate. Then, a solution of the obtained ethyl 2-[(2′-cyano-2-methoxybiphenyl-4-yl)methyl]-3-oxohexanoate, ethanimidamide hydrochloride (3.25 g) and 28% sodium methoxide (9.91 g) in methanol (70 mL) was stirred overnight. The solvent was evaporated under reduced pressure, and saturated aqueous ammonium chloride solution was added to the residue. The precipitated solid was collected by filtration, and washed with water and diethyl ether to give the title compound (5.63 g, 52%) as a white solid.

Aufarbeitung

  1. customThe solvent was evaporated under reduced pressure, and saturated aqueous ammonium chloride solution
  2. additionwas added to the residue
  3. filtrationThe precipitated solid was collected by filtration
  4. washwashed with water and diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-7557209e17a2442eab881d6d768dadbf
Quelldatensatz
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07998968B2

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