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

HRID 1671769

Reaction equation

HRID 1671769 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

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

Conditions

Temperature
0 °C

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-48a876d6194d42e6a772d7d4ea153860
Source dataset
uspto-grants-2011_08
Patent number
US07994317B2

Linked notes

Loading…