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

HRID 1422475Notes

Reaction equation

HRID 1422475 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-21a1f1f5ab624e4c9d0d538b6c42ea35
Source dataset
uspto-grants-2015_01
Patent number
US08927281B2

Reaction notes

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