Methylamine → 4-Chloro-N-methyl-6-(4-methylpiperazin-1-yl)-1,3,5-triazin-2-amine

HRID 1671769

Reaktionsgleichung

Reaktionsgleichung von HRID 1671769
[N:1]1[C:8](Cl)=[N:7][C:5](Cl)=[N:4][C:2]=1[Cl:3].[CH3:10][NH2:11].[OH-].[Na+].[CH3:14][N:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1>CC#N.O>[Cl:3][C:2]1[N:1]=[C:8]([N:18]2[CH2:19][CH2:20][N:15]([CH3:14])[CH2:16][CH2:17]2)[N:7]=[C:5]([NH:11][CH3:10])[N:4]=1

Komponenten

6

Edukt 4

HCID 6329Methylamine2×HCID 7954Cyanuric chlorideHCID 14798Sodium Hydroxide2×HCID 531671-Methylpiperazine

Produkt 1

HCID 807675004-Chloro-N-methyl-6-(4-methylpiperazin-1-yl)-1,3,5-triazin-2-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 18373917Acetonitrile--water (1/1)Lösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A mixture of cyanuric chloride (3.86 g, 20.9 mmol, 1 equivalent) in CH3CN/H2O (1/1, 200 ml) was cooled to 0° C. Methylamine solution in water (40% (w), 1.83 ml, 20.9 mmol, 1 equivalent) was added, followed by 1N NaOH (20.9 ml, 20.9 mmol, 1 equivalent). The reaction mixture was stirred at 0° C. for 15 min and LCMS showed the reaction had completed. At 0° C., N-methylpiperazine (2.3 ml, 20.9 mmol, 1 equivalent) was added, followed by 1N NaOH (4.2 ml, 0.2 equivalents). The solution turned to clear. The solvent was evaporated to give the crude product which was further purified with silica gel chromatography (eluant 70% B, solvent B is 10% MeOH in DCM with 1% Et3N) to give the product (1.8 g). 1H NMR (CDCl3, 400 MHz): δ2.33 (s, 3H), 2.44 (br, 4H), 2.95&2.96 (3H), 3.86 (br, 4H), 5.1&5.7 (br, 1H).

Aufarbeitung

  1. customThe solvent was evaporated
  2. customto give the crude product which
  3. customwas further purified with silica gel chromatography (eluant 70% B, solvent B is 10% MeOH in DCM with 1% Et3N)

Quellen und Nachweise

ORD-Eintrag
ord-48a876d6194d42e6a772d7d4ea153860
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07994317B2

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