Triethylamine → 6-Chloro-N4-(3-nitrobenzyl)pyrimidine-2,4,5-triamine

HRID 723430

Reaktionsgleichung

Reaktionsgleichung von HRID 723430
Cl[C:2]1[C:7]([NH2:8])=[C:6]([Cl:9])[N:5]=[C:4]([NH2:10])[N:3]=1.Cl.[N+:12]([C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH2:18][NH2:19])([O-:14])=[O:13].C(N(CC)CC)C>CCCCO>[Cl:9][C:6]1[N:5]=[C:4]([NH2:10])[N:3]=[C:2]([NH:19][CH2:18][C:17]2[CH:20]=[CH:21][CH:22]=[C:15]([N+:12]([O-:14])=[O:13])[CH:16]=2)[C:7]=1[NH2:8]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 3010392,5-Diamino-4,6-dichloropyrimidineHCID 2724030Benzenemethanamine, 3-nitro-, hydrochloride (1:1)

Produkt 1

HCID 866110486-Chloro-N4-(3-nitrobenzyl)pyrimidine-2,4,5-triamineAusbeute 78,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2631-ButanolLösungsmittel

Versuchsvorschrift

A mixture of 4,6-dichloropyrimidine-2,5-diamine (700 mg, 3.91 mmol), 3-nitrobenzylamine hydrochloride (885 mg, 4.69 mmol) and triethylamine (1.6 mL, 11.7 mmol) in n-BuOH (20 mL) was refluxed for 17 h, concentrated in vacuo and the residue partitioned between EtOAc (10 mL) and H2O (5 mL). The organic phase was dried (MgSO4) and concentrated in vacuo to give the title compound as an orange solid (906 mg, 76%) which was used in the next reaction without further purification; NMR δH (400 MHz, CDCl3) 8.16 (1H, s), 8.10 (1H, d, J 8.0 Hz), 7.80 (1H, d, J 7.5 Hz), 7.62 (1H, t, J 7.5 Hz), 7.25 (1H, t, J 6.0 Hz), 5.69 (2H, s), 4.67 (2H, d, J 6.0 Hz) and 3.93 (2H, br s).

Aufarbeitung

  1. temperaturewas refluxed for 17 h
  2. concentrationconcentrated in vacuo
  3. customthe residue partitioned between EtOAc (10 mL) and H2O (5 mL)
  4. dry with materialThe organic phase was dried (MgSO4)
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-cb33c0f8c8b24b3da04a480ad70e26d4
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07141575B2

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