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

HRID 1671769

反応式

HRID 1671769 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

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

反応条件

温度
0 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-48a876d6194d42e6a772d7d4ea153860
出典データセット
uspto-grants-2011_08
特許番号
US07994317B2

関連ノート

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