3-Nitroaniline → 4-N-(3-aminophenyl)pyrido[4,3-d]pyrimidine-4,7-diamine

HRID 50787

Reaktionsgleichung

Reaktionsgleichung von HRID 50787
[NH2:1][C:2]1[N:11]=[CH:10][C:9]2[C:8](SC)=[N:7][CH:6]=[N:5][C:4]=2[CH:3]=1.[N+:14]([C:17]1[CH:18]=[C:19]([CH:21]=[CH:22][CH:23]=1)[NH2:20])([O-])=O>CO.C1COCC1.[Pd]>[NH2:1][C:2]1[N:11]=[CH:10][C:9]2[C:8]([NH:14][C:17]3[CH:23]=[CH:22][CH:21]=[C:19]([NH2:20])[CH:18]=3)=[N:7][CH:6]=[N:5][C:4]=2[CH:3]=1

Komponenten

5

Edukt 2

HCID 74233-NitroanilineHCID 104425627-Amino-4-methylthiopyrido[4,3-d]pyrimidine

Produkt 1

HCID 53280644-N-(3-aminophenyl)pyrido[4,3-d]pyrimidine-4,7-diamineAusbeute 16,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 21899815MeOH tetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
200 °C

Versuchsvorschrift

A mixture of 7-amino-4-methylthiopyrido[4,3-d]pyrimidine (307 mg, 1.60 mmol) (described in a previous experimental) and 3-nitroaniline (2.00 g, 14.5 mmol) is stirred at 200° C. for 1.5 h, and the crude product is suspended in MeOH/THF (4:1, 250 mL) and hydrogenated over 5% Pd/C (2 g) at 60 psi and 20° C. for 24 h. The solution is filtered over celite, washing thoroughly (hot MeOH), and is then absorbed onto alumina and chromatographed on alumina (4-8% EtOH/CHCl3) to give 7-amino-4-(3-aminoanilino)pyrido[4,3-d]pyrimidine (66 mg, 16%) as a green solid,. 1H NMR (DMSO) δ 9.57 (1H, brs), 9.30 (1H, s), 8.33 (1H, s), 7.04 (1H, t, J=2.0 Hz), 6.99 (1H, t, J=8.0 Hz), 6.88 (1H, brd, J=8.0 Hz), 6.55 (2H, brs), 6.40 (1H, s), 6.34 (1H, dd, J=7.9, 1.3 Hz), 5.10 (2H, brs).

Aufarbeitung

  1. filtrationThe solution is filtered over celite
  2. washwashing thoroughly (hot MeOH)
  3. customis then absorbed onto alumina
  4. customchromatographed on alumina (4-8% EtOH/CHCl3)

Quellen und Nachweise

ORD-Eintrag
ord-4f393b45b49743bbbb80791aeb389193
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06713484B2

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