title: Syntheses of (3) H-labeled, (14) C-labeled, and (2) H4 -labeled SCH 444877, phosphodiesterase type 5 inhibitors.
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%.
authors.affiliation: Merck Research Laboratories, 126 E. Lincoln Avenue, PO Box 2000, Rahway, NJ, 07065, USA.
authors.forename: Sumei
authors.initials: S
authors.lastname: Ren
authors.forename: David
authors.initials: D
authors.lastname: Hesk
authors.forename: Paul
authors.initials: P
authors.lastname: McNamara
authors.forename: David
authors.initials: D
authors.lastname: Koharski
authors.forename: Sharon
authors.initials: S
authors.lastname: Hendershot
mesh_terms: D002250:Carbon Radioisotopes / Q000737:chemistry; D060326:Chemistry Techniques, Synthetic; D003903:Deuterium / Q000737:chemistry*; D006147:Guanine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D007093:Imidazoles / Q000138:chemical synthesis* / Q000737:chemistry*; D007553:Isotope Labeling; D058986:Phosphodiesterase 5 Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry*; D012015:Reference Standards; D014316:Tritium / Q000737:chemistry*
chemical_list: C000590220:3-(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; D002250:Carbon Radioisotopes; D007093:Imidazoles; D058986:Phosphodiesterase 5 Inhibitors; D014316:Tritium; D006147:Guanine; D003903:Deuterium
keywords: PDE 5 inhibitor; SCH 444877; carbon-14; deuterium; synthesis; tritium