Aniline → HCID 89781929, Verbindung

HRID 1056076

Reaktionsgleichung

[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[Br:11][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:21]=1[N:20]=[C:19](Cl)[N:18]=[CH:17]2.[NH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[NH4+].[Cl-]>C1COCC1>[Br:11][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:21]=1[N:20]=[C:19]([NH:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[N:18]=[CH:17]2

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

LHMDS (1.0M in THF; 4.11 mL, 4.11 mmol) was added to a solution of 8-bromo-2-chloroquinazoline (Ark Pharm, Inc., Libertyville, Ill.; 500 mg, 2.053 mmol) and aniline (0.337 mL, 3.70 mmol) in THF (10 mL) at 0° C., and the resulting solution was stirred at 0° C. for 10 min. Saturated aq. NH4Cl (10 mL) was added, and the resulting mixture was partitioned between EtOAc (50 mL) and additional saturated aq. NH4Cl (30 mL). The organic layer was separated, washed with brine (30 mL), dried over Na2SO4, filtered and concentrated in vacuo. Chromatographic purification of the residue (silica gel, 0-10% MeOH/DCM) furnished 8-bromo-N-phenylquinazolin-2-amine (616 mg, 2.052 mmol, 100% yield) as a yellow solid: m/z (ESI, +ve) 300.0 (M+H)+.

Aufarbeitung

customthe resulting mixture was partitioned between EtOAc (50 mL) and additional saturated aq. NH4Cl (30 mL)
customThe organic layer was separated
washwashed with brine (30 mL)
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customChromatographic purification of the residue (silica gel, 0-10% MeOH/DCM)

Quellen und Nachweise

ORD-Eintrag: ord-186b83400f264668b58b6ad833df54ab
Quelldatensatz: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09394297B2

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