Ammonium Chloride → HCID 86713569, Verbindung

HRID 524041Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 524041
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[CH:31]=[N:30][C:14]3[N:15]=[C:16]([NH:19][C:20]4[C:25]([N+:26]([O-])=O)=[CH:24][CH:23]=[CH:22][C:21]=4[CH3:29])[N:17]=[CH:18][C:13]=3[CH:12]=2)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.[Cl-].[NH4+]>C(O)C.O.[Fe]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[CH:31]=[N:30][C:14]3[N:15]=[C:16]([NH:19][C:20]4[C:25]([NH2:26])=[CH:24][CH:23]=[CH:22][C:21]=4[CH3:29])[N:17]=[CH:18][C:13]=3[CH:12]=2)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1

Komponenten

6

Edukt 2

HCID 25517Ammonium ChlorideHCID 86713568HCID 86713568, Verbindung

Produkt 1

HCID 86713569HCID 86713569, VerbindungAusbeute 32 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23925IronKatalysatorHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of 6-(3,5-dimethoxyphenyl)-N-(2-methyl-6-nitrophenyl)pyrido[2,3-d]pyrimidin-2-amine (100 mg, 0.24 mmol) in ethanol (5 mL) and water (5 mL) was added iron powder (110 mg, 1.92 mmol) and ammonium chloride (100 mg, 1.920 mmol). The mixture was stirred at 100° C. for 1 hour, cooled to RT, filtered and concentrated. The residue was purified by Preparative HPLC to afford N1-(6-(3,5-dimethoxyphenyl)pyrido[2,3-d]pyrimidin-2-yl)-6-methylbenzene-1,2-diamine (29.5 mg, 32%) as a yellow solid. MS (ES+) C22H21N5O2 requires: 387. found: 388 [M+H]+; 1H-NMR (500 MHz, DMSO-d6) δ ppm 9.30, 9.21 (br, br, 2H), 8.95 (s, 1H), 8.60 (d, 1H, J=3.0 Hz), 6.96-6.92 (m, 3H), 6.63 (d, 1H, J=5.5 Hz), 6.55 (t, 1H, J=2.0 Hz), 6.50-6.48 (m, 1H), 4.79 (s, 2H), 3.84 (s, 6H), 2.08 (s, 3H).

Aufarbeitung

  1. temperaturecooled to RT
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customThe residue was purified by Preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-e36a4d419fac426cb2ffb36d30f0ad89
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09340514B2

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