Reaction #1509652

Reaction equation

2,6-dichloro-9-isopropyl-9H-purine

tyramine

→

title compound

4-(2-(2-chloro-9-isopropyl-9H-purin-6-ylamino)ethyl)phenol

Solvents

i-PrOH

Conditions

Workup

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

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.

Source