Potassium Iodide → HCID 178470277, Verbindung

HRID 625735

Reaktionsgleichung

Reaktionsgleichung von HRID 625735
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[N:3]=1.[I-].[K+].CCN(C(C)C)C(C)C.[NH:28]1[CH:32]=[CH:31][C:30]([NH2:33])=[N:29]1>CN(C=O)C.O>[NH:28]1[CH:32]=[CH:31][C:30]([NH:33][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=[C:4]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[N:3]=2)=[N:29]1

Komponenten

7

Edukt 4

HCID 4875Potassium IodideHCID 81531DiisopropylethylamineHCID 3477840Ethyl 4-chloroquinazoline-2-carboxylateHCID 178418806HCID 178418806, Verbindung

Produkt 1

HCID 178470277HCID 178470277, VerbindungAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of ethyl 4-chloroquinazoline-2-carboxylate (0.250 g, 1.05 mmol) in DMF (2.5 mL) at rt under argon were added potassium iodide (0.192 g, 1.16 mmol), DIEA (0.238 mL, 1.37 mmol), and 1H-pyrazol-3-amine (0.113 g, 1.37 mmol). The mixture was stirred at rt for 5 h and diluted with H2O (5 mL). The precipitate was collected by filtration, washed with H2O, and dried under high vacuum for several hours to afford ethyl 4-(1H-pyrazol-3-ylamino)quinazoline-2-carboxylate as a tan solid (0.190 g, 64%). 1H NMR (300 MHz, DMSO-d6) δ 12.52 (s, 1H), 10.58 (s, 1H), 8.72 (d, 1H), 7.90 (d, 2H), 7.78 (s, 1H), 7.68 (m, 1H), 7.18 (s, 1H), 4.48 (q, 2H), 1.48 (t, 3H); LC-MS (ESI) m/z 284 (M+H)+.

Aufarbeitung

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with H2O
  3. customdried under high vacuum for several hours

Quellen und Nachweise

ORD-Eintrag
ord-272ad29a4a6f4813943c8935fda8451f
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09308207B2

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