Sodium Cyanide → 4-[(4-Methoxyphenyl)(methyl)amino]quinazoline-2-carbonitrile

HRID 1876152Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1876152
Cl.Cl[C:3]1[N:12]=[C:11]([N:13]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[CH3:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1.[C-]#N.[Na+].[N:26]12CCN(CC1)C[CH2:27]2>CS(C)=O.CC(O)C.O.C(OCC)(=O)C>[CH3:22][O:21][C:18]1[CH:19]=[CH:20][C:15]([N:13]([CH3:14])[C:11]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[N:4]=[C:3]([C:27]#[N:26])[N:12]=2)=[CH:16][CH:17]=1

Komponenten

8

Edukt 3

HCID 8929Sodium CyanideHCID 9237DabcoHCID 86639964(2-Chloroquinazolin-4-yl)-(4-methoxyphenyl)-methylamine hydrochloride

Produkt 1

HCID 575165474-[(4-Methoxyphenyl)(methyl)amino]quinazoline-2-carbonitrileAusbeute 139,4 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittelHCID 3776IsopropanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
35 °C

Versuchsvorschrift

To a solution of (2-chloroquinazolin-4-yl)-(4-methoxyphenyl)-methylamine hydrochloride (56 mg, 0.17 mmol) in 1 mL of DMSO and 0.5 mL of 2-propanol were added sodium cyanide (16 mg, 0.34 mmol) and 1,4-diazabicyclo[2.2.2]octane (9 mg, 0.084 mmol). The mixture was heated at 35° C. for 1 d with stirring. The solution was diluted with 5 mL of water and 10 mL of ethyl acetate. The organic layer was washed with water, then dried and concentrated. The resulting crude material was purified by silica gel column chromatography to give the title compound (34 mg, 70%). 1H NMR (CDCl3, 400 MHz) δ 7.85 (d, 1H, J=8.4 Hz), 7.64 (t, 1H, J=6.8 Hz), 7.14 (m, 3H), 6.96 (m, 3H), 3.86 (s, 3H), 3.61 (s, 3H); ESI-MS m/z 291 (M+H)+.

Aufarbeitung

  1. washThe organic layer was washed with water
  2. customdried
  3. concentrationconcentrated
  4. customThe resulting crude material was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-bfb59ba6a15e49e489559cf83a4456ce
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08309562B2

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