Water → 2-Chloro-N-[4-chloro-6-(4-chlorophenylamino)-pyrimidin-5-yl]-benzamide

HRID 1246782

Reaktionsgleichung

[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)[C:3]=1[NH2:16].[Cl:17][C:18]1[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20](Cl)=[O:21].O>CN(C)C(=O)C>[Cl:17][C:18]1[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20]([NH:16][C:3]1[C:2]([Cl:1])=[N:7][CH:6]=[N:5][C:4]=1[NH:8][C:9]1[CH:10]=[CH:11][C:12]([Cl:15])=[CH:13][CH:14]=1)=[O:21]

Komponenten

Reaktionsbedingungen

Temperatur: 5 °C

Versuchsvorschrift

6-Chloro-N4-(4-chlorophenyl)-pyrimidine-4,5-diamine I-(1A-1)a (1.00 g, 3.92 mmol) was dissolved in 6 ml of N,N-dimethylacetamide giving a clear brown solution. After cooling to 5° C., neat 2-chlorobenzoyl chloride (0.80 g, 4.34 mmol) was added over 1 minute. The solution was warmed to room temperature and stirred for 4 hours. Addition of water (15 ml) caused white precipitate to come out of solution. The mixture was stirred for an additional 30 minutes at room temperature, then the precipitate was collected by vacuum filtration, rinsing with H2O and then hexanes. The solid was further dried under vacuum to give I-(4A-7)a as a colorless solid (1.27 g, 82%): +ACPI MS (M+1) 393.1; 1H NMR (400 MHz, DMSO-d6) δ 10.02 (s, 1H), 9.11 (s, 1H), 8.40 (s, 1H), 7.93 (dd, J=7.4, 1.6 Hz, 1H), 7.66–7.40 (m, 7H).

Aufarbeitung

temperatureThe solution was warmed to room temperature
stirringThe mixture was stirred for an additional 30 minutes at room temperature
filtrationthe precipitate was collected by vacuum filtration
washrinsing with H2O
customThe solid was further dried under vacuum

Quellen und Nachweise

ORD-Eintrag: ord-08f07784aef941d5ba0e1c817d2762cd
Quelldatensatz: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07129239B2

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