Tyramine → 4-(2-((2-Chloro-9-isopropyl-9H-purin-6-yl)amino)ethyl)phenol

HRID 1422475노트

반응식

HRID 1422475 반응식
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH:11]([CH3:13])[CH3:12])=[C:4](Cl)[N:3]=1.[NH2:15][CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=1.C(N(CC)CC)C>CC(O)C>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH:11]([CH3:13])[CH3:12])=[C:4]([NH:15][CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=2)[N:3]=1

참가 물질

5

반응물 3

HCID 5610TyramineHCID 8471TriethylamineHCID 112184902,6-dichloro-9-(propan-2-yl)-9H-purine

생성물 1

HCID 755299704-(2-((2-Chloro-9-isopropyl-9H-purin-6-yl)amino)ethyl)phenol

시약·촉매·용매 1

HCID 3776Isopropanol용매

실험 절차

2,6-dichloro-9-isopropyl-9H-purine (500 g) was added in portions to a stirred mixture of tyramine (593 g), triethylamine (262 g), and i-PrOH (5.0 L) at 50° C. The mixture was stirred at that temperature for 4 hr, then the reaction mixture was concentrated. The residue was taken up in isopropyl acetate (6.0 L) and was washed with 20% citric acid solution (2.0 L) and water (2.0 L). The organic layer was concentrated to dryness, then was taken up in ethanol (2.0 L) and again concentrated to dryness. The crude solid was crystallized from ethanol (3.2 L) to provide the title compound as a solid.

후처리

  1. concentrationthe reaction mixture was concentrated
  2. washwas washed with 20% citric acid solution (2.0 L) and water (2.0 L)
  3. concentrationThe organic layer was concentrated to dryness
  4. concentrationagain concentrated to dryness
  5. customThe crude solid was crystallized from ethanol (3.2 L)

출처 및 근거

ORD 기록
ord-21a1f1f5ab624e4c9d0d538b6c42ea35
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08927281B2

반응 노트

불러오는 중…