Propyl isocyanate → 4-(dimethylamino-methyleneamino)-5-fluoro-2-oxo-2H-pyrimidine-1-carboxylic acid propylamide

HRID 1038948Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1038948
[F:1][C:2]1[C:3]([N:9]=[CH:10][N:11]([CH3:13])[CH3:12])=[N:4][C:5]([OH:8])=[N:6][CH:7]=1.[CH2:14]([N:17]=[C:18]=[O:19])[CH2:15][CH3:16]>ClCCl>[CH2:14]([NH:17][C:18]([N:6]1[CH:7]=[C:2]([F:1])[C:3]([N:9]=[CH:10][N:11]([CH3:13])[CH3:12])=[N:4][C:5]1=[O:8])=[O:19])[CH2:15][CH3:16]

Komponenten

4

Edukt 2

HCID 61033Propyl isocyanateHCID 178484257HCID 178484257, Verbindung

Produkt 1

HCID 508983554-(dimethylamino-methyleneamino)-5-fluoro-2-oxo-2H-pyrimidine-1-carboxylic acid propylamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a 7 milliliter (mL) screw-cap vial were added dichloromethane (CH2Cl2; 5 milliliters (mL)), N′-(5-fluoro-2-hydroxy-pyrimidin-4-yl)-N,N-dimethylformamidine (200 milligrams (mg), 1.09 millimoles (mmol)), and propyl isocyanate (94 mg, 1.10 mmol). The mixture was shaken at room temperature for 16 hours (h). After evaporation and recrystallization of the crude product from CH2Cl2 and heptane, the title compound was isolated as a white solid (274 mg, 94%): mp 266-268° C.; 1H NMR (300 MHz, CDCl3) δ10.42 (br s, 1H), 8.84 (s, 1H), 8.46 (d, J=6.6 Hz, 1H), 3.39-3.30 (m, 2H), 3.25 (s, 6H), 1.70-1.57 (m, 2H), 0.97 (t, J=7.4 Hz, 3H); ESIMS m/z 270 ([M+H]+).

Aufarbeitung

  1. customTo a 7 milliliter (mL) screw-cap vial
  2. customAfter evaporation and recrystallization of the crude product from CH2Cl2 and heptane

Quellen und Nachweise

ORD-Eintrag
ord-9af78ea029b84d3397f87e23a488e18d
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08552020B2

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