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

HRID 1422470Notes

Reaction equation

HRID 1422470 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>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

4

Reactant 2

HCID 5610TyramineHCID 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 (1.1 mmol) was mixed with tyramine (1.16 mmol) dissolved in i-PrOH (6 ml) and the mixture was stirred overnight. The reaction mixture was concentrated, and the residue purified by column chromatography on silica gel, eluting with hexane/EtOAc (5:1 to 1:2) to afford the title compound as a white solid. 1H NMR (500 MHz, CDCl3): δ 9.21 (br, 1H), 8.49 (s, 1H), 7.80 (s, 1H), 7.10 (d, 2H), 6.73 (d, 2H), 4.87 (m, 1H), 4.03 (t, 2H), 3.01 (t, 2H), 1.68 (d, 6H); HRMS (EI) calcd for C16H18ClN5O (M+H±) 332.1273, found 332.1278.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue purified by column chromatography on silica gel
  3. washeluting with hexane/EtOAc (5:1 to 1:2)

Sources & evidence

ORD record
ord-ad4e5badbba84af4a0f0924f6f325e7d
Source dataset
uspto-grants-2015_01
Patent number
US08927281B2

Reaction notes

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