Syntheses of (3) H-labeled, (14) C-labeled, and (2) H4 -labeled SCH 444877, phosphodiesterase type 5 inhibitors

J Labelled Comp Radiopharm. 2013 Jul-Aug;56(9-10):480-4. doi: 10.1002/jlcr.3080. Epub 2013 Aug 24.

Abstract

The syntheses of [(3) H]SCH 444877, [(2) H4 ]SCH 444877, and [(14) C]SCH 444877 are described. [(3) H]SCH 444877 was prepared in three steps from tritium gas. [(2) H4 ]SCH 444877 was synthesized from [(2) H4 ]ethanolamine in four steps with an overall yield of 40%. [(14) C]SCH 444877 was prepared from barium [(14) C]cyanamide in 10 steps with an overall yield of 8.1%.

Keywords: PDE 5 inhibitor; SCH 444877; carbon-14; deuterium; synthesis; tritium.

MeSH terms

  • Carbon Radioisotopes / chemistry
  • Chemistry Techniques, Synthetic
  • Deuterium / chemistry*
  • Guanine / analogs & derivatives*
  • Guanine / chemical synthesis
  • Guanine / chemistry
  • Imidazoles / chemical synthesis*
  • Imidazoles / chemistry*
  • Isotope Labeling
  • Phosphodiesterase 5 Inhibitors / chemical synthesis*
  • Phosphodiesterase 5 Inhibitors / chemistry*
  • Reference Standards
  • Tritium / chemistry*

Substances

  • 3-(3-chloro-4-methoxybenzyl)-2-((tetrahydro-2H-pyran-4-yl)amino)-5-ethyl-7,8-dihydro-3H-imidazo(2,1-b)purin-4(5H)-one
  • Carbon Radioisotopes
  • Imidazoles
  • Phosphodiesterase 5 Inhibitors
  • Tritium
  • Guanine
  • Deuterium