Phosphorus oxychloride → 7-(Benzyloxy)-4-chloro-6-methoxyquinazoline

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Reaktionsgleichung

[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13](O)=[N:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:20][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:24])=O>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([Cl:24])=[N:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:20][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

Reaktionsbedingungen

Temperatur: 120 °C

Versuchsvorschrift

A stirred mixture of 7-(benzyloxy)-6-methoxyquinazolin-4-ol (5.10 g, 18.09 mmol) and phosphorous oxychloride (10 mL, 109 mmol) in dry toluene (30 mL), was heated to 120° C. for 2 h. After cooling to room temperature the mixture was concentrated under reduced pressure. The residue was dissolved in ethyl acetate (200 mL) and washed with sat aqueous NaHCO3 solution (2×100 mL). The organic layer was separated and dried over MgSO4 then concentrated under reduced pressure to afford 7-(benzyloxy)-4-chloro-6-methoxyquinazoline as a cream solid (3.89 g, 72%) which was taken into the next step without further purification. 1H NMR (300 MHz, CDCl3) δ 8.85 (s, 1H), 7.49 (m, 2H), 7.33-7.43 (m, 5H), 5.33 (s, 2H), 4.07 (s, 3H); LC-MS (ESI) m/z 301 (M+H)+.

Aufarbeitung

temperatureAfter cooling to room temperature the mixture
concentrationwas concentrated under reduced pressure
dissolutionThe residue was dissolved in ethyl acetate (200 mL)
washwashed
customThe organic layer was separated
dry with materialdried over MgSO4
concentrationthen concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag: ord-9f1af7b0cdeb451e81fc746e25ae9dea
Quelldatensatz: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09320739B2

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