Ammonium Chloride → HCID 86713570, Verbindung

HRID 2274186Notizen

Reaktionsgleichung

[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([O:10][CH3:11])=[C:4]([Cl:12])[C:3]=1[C:13]1[CH:33]=[N:32][C:16]2[N:17]=[C:18]([NH:21][C:22]3[C:27]([N+:28]([O-])=O)=[CH:26][CH:25]=[CH:24][C:23]=3[CH3:31])[N:19]=[CH:20][C:15]=2[CH:14]=1.[Cl-].[NH4+]>C(O)C.O.[Fe]>[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([O:10][CH3:11])=[C:4]([Cl:12])[C:3]=1[C:13]1[CH:33]=[N:32][C:16]2[N:17]=[C:18]([NH:21][C:22]3[C:27]([NH2:28])=[CH:26][CH:25]=[CH:24][C:23]=3[CH3:31])[N:19]=[CH:20][C:15]=2[CH:14]=1

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

To a solution of 6-(2,6-dichloro-3,5-dimethoxyphenyl)-N-(2-methyl-6-nitrophenyl)pyrido[2,3-d]pyrimidin-2-amine (80 mg, 0.168 mmol) in ethanol (4 mL) and water (4 mL) was added iron powder (75 mg, 1.344 mmol) and ammonium chloride (74 mg, 1.344 mmol). The mixture was stirred at 100° C. for 2 hrs, cooled to RT, filtered and concentrated. The residue was purified by silica gel column chromatography (ethyl acetate:petroleum ether=4:1) to afford N1-(6-(2,6-dichloro-3,5-dimethoxyphenyl)pyrido[2,3-d]pyrimidin-2-yl)-6-methylbenzene-1,2-diamine (40 mg, 53%) as a yellow solid. MS (ES+) C22H19Cl2N5O2 requires: 455, 457. Found: 456, 458 [M+H]+. 1H-NMR (400 MHz, DMSO-d6) δ ppm 9.33 (br. s., 1H), 9.01 (s, 1H), 9.65 (br. s., 1H), 8.23 (s, 1H), 7.05 (s, 1H), 6.93 (br. s., 1H), 6.64-6.63 (m, 1H), 6.50-6.49 (m, 1H), 4.80 (s, 2H), 3.99 (s, 6H), 2.09 (s, 3H).

Aufarbeitung

temperaturecooled to RT
filtrationfiltered
concentrationconcentrated
customThe residue was purified by silica gel column chromatography (ethyl acetate:petroleum ether=4:1)

Quellen und Nachweise

ORD-Eintrag: ord-3d8cd16ba0bd44bbb502105ba44dccf9
Quelldatensatz: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09126951B2

Notizen zur Reaktion

Wird geladen…