Dimethylformamide → HCID 86703935, Verbindung

HRID 1049938Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1049938
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10](I)[CH:11]=1)[N:8]=[CH:7][N:6]=[C:5]2[NH2:13].[CH3:14][N:15](C)C=O>ClCCl.O.[C-]#N.[Zn+2].[C-]#N.[Pd]>[NH2:13][C:5]1[C:4]2[C:9](=[C:10]([C:14]#[N:15])[CH:11]=[C:2]([Cl:1])[CH:3]=2)[N:8]=[CH:7][N:6]=1

Komponenten

7

Edukt 2

HCID 6228DimethylformamideHCID 86703934HCID 86703934, Verbindung

Produkt 1

HCID 86703935HCID 86703935, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 11186Zinc cyanide (Zn(CN)2)KatalysatorHCID 23938PalladiumKatalysatorHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

To an 8 mL screw-cap vial was added 6-chloro-8-iodo-quinazolin-4-amine (450 mg, 1.47 mmol), dimethylformamide (2 mL), zinc cyanide (0.65 equiv., 1.0 mmol, 115 mg), and palladium tetra is(triphenylphosphine), (0.1 equiv., 0.15 mmol), 179 mg). The reaction was capped and shaken at 110° C. overnight. The reaction was cooled to room temperature, diluted with 3 mL of dichloromethane, and 2 mL of water was added. The precipitate that followed was collected by filtration, and washed with water, then dichloromethane yielding 240 mg of 4-amino-6-chloro-quinazoline-8-carbonitrile as a light yellow solid. 1H NMR (400 MHz, DMSO) δ 8.72-8.67 (d, J=2.2 Hz, 1H), 8.54-8.50 (s, 1H), 8.50-8.46 (d, J=2.1 Hz, 1H), 8.29-8.22 (bs, 2H). LCMS M/Z (M+H)=205.

Aufarbeitung

  1. customTo an 8 mL screw-cap vial
  2. customThe reaction was capped
  3. temperatureThe reaction was cooled to room temperature
  4. additionwas added
  5. filtrationThe precipitate that followed was collected by filtration
  6. washwashed with water

Quellen und Nachweise

ORD-Eintrag
ord-c5f17549b3104f8b99210cd392333558
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09382241B2

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