Diglyme → 6-(2-Fluoro-4-nitrophenoxy)-N-(4-methoxybenzyl)pyrimidin-4-amine

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Reaktionsgleichung

[CH3:1][O:2][C:3]1[CH:17]=[CH:16][C:6]([CH2:7][NH:8][C:9]2[CH:14]=[C:13](Cl)[N:12]=[CH:11][N:10]=2)=[CH:5][CH:4]=1.[F:18][C:19]1[CH:24]=[C:23]([N+:25]([O-:27])=[O:26])[CH:22]=[CH:21][C:20]=1[OH:28].CCN(C(C)C)C(C)C.COCCOCCOC>CCOC(C)=O>[CH3:1][O:2][C:3]1[CH:17]=[CH:16][C:6]([CH2:7][NH:8][C:9]2[CH:14]=[C:13]([O:28][C:20]3[CH:21]=[CH:22][C:23]([N+:25]([O-:27])=[O:26])=[CH:24][C:19]=3[F:18])[N:12]=[CH:11][N:10]=2)=[CH:5][CH:4]=1

Komponenten

Reaktionsbedingungen

Temperatur: 160 °C

Versuchsvorschrift

A mixture of N-(4-methoxybenzyl)-6-chloropyrimidin-4-amine (2.3 g, 9.2 mmol), 2-fluoro-4-nitrophenol (1.45 g, 9.2 mmol), DIPEA (15 mL), and 2-methoxyethyl ether (75 mL) was heated at 160° C. in a sealed pressure bottle for 50 h. The mixture was cooled, poured onto crushed ice (200 g), treated with EtOAc (200 mL). After vigorously stirring for 10 min, the insoluble material was filtered off. The EtOAc phase was washed with saturated aq. Na2CO3 solution (100 mL), brine (3×100 mL), dried (MgSO4) and concentrated in vacuo. The gummy solid obtained was triturated with isopropyl ether to give the title compound (1.75 g, 76%) as a brown solid. 1H NMR (DMSO-d6) δ 8.32 (dd, 1H, J=10.2, 2.0 Hz), 8.15 (d, 2H, J=9.2 Hz), 8.05 (br s, 1H), 7.61 (dd, 1H, J=8.4, 8.4 Hz), 7.26 (d, 2H, J=8.5 Hz), 6.91 (d, 2H, J=8.5 Hz), 6.14 (br s, 1H), 4.48 (br s, 2H), 3.74 (s, 3H).

Aufarbeitung

temperatureThe mixture was cooled
additionpoured
filtrationthe insoluble material was filtered off
washThe EtOAc phase was washed with saturated aq. Na2CO3 solution (100 mL), brine (3×100 mL)
dry with materialdried (MgSO4)
concentrationconcentrated in vacuo
customThe gummy solid obtained
customwas triturated with isopropyl ether

Quellen und Nachweise

ORD-Eintrag: ord-9c5c50bbff74400e86ed180350812a0b
Quelldatensatz: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07714138B2

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