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

HRID 1671769

반응식

HRID 1671769 반응식
[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

참가 물질

6

반응물 4

HCID 6329Methylamine2회HCID 7954Cyanuric chlorideHCID 14798Sodium Hydroxide2회HCID 531671-Methylpiperazine

생성물 1

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

시약·촉매·용매 1

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

반응 조건

온도
0 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-48a876d6194d42e6a772d7d4ea153860
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07994317B2

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