A novel synthesis of guanine PDE inhibitors via tricyclic imidazopyrimidines

Tetrahedron Letters

Volumn 44, Issue 13, 2003, Pages 2721-2723

  Gala, Dinesh ^a   DiBenedetto, Donald J ^a   Kugelman, Max ^a   Mitchell, Michael B ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

GUANINE DERIVATIVE; IMIDAZOPYRIDINE DERIVATIVE; PHOSPHODIESTERASE INHIBITOR;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0037463725     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00383-6     Document Type: Article

References (14)

1. Ahn H.-S., Czarniecki M., et al. J. Med. Chem. 40:1997;2196.
2. Vemulapalli S., Watkins R.W., Chintala M., Davis H., Ahn H.-S., Fawi A., Tulshian D., Chiu P., Chatterjee M., Lin C.-C., Sybertz E.J. J. Cardiovasc. Pharmacol. 28:1996;862.
3. Gala D., DiBenedetto D.J., Kugleman M., Puar M.S. Tetrahedron Lett. 44:2003;2717-2720.
4. Gala D., DiBenedetto D., Gunter F., Kugelman M., Maloney D., Cordero M., Mergelsberg I. Org. Process Res. Development. 1:1996;163.
5. Pfleiderer W. Ber. 1957;2272.
6. Roehrkasten R., Raatz P., Kerher R.P., Blaszkewicz M. Zeitschrift fuer Naturforschung B: Chemical. 52:1997;1526-1532.
7. Low J.N., Scrimgeour S.N., Egglishaw C., Howie R.A., Moreno-Carretero M.N., Hueso-Urena F. Communications. 50:1994;1329.
8. For the preparation of Cyclopentylamino alcohol, see: (a) Barnard, H. Can. J. Chem. 1958, 36, 1252; (b) Overman, L. E.; Sugai, S. J. Org. Chem. 1985, 50, 4154; (c) Barr, A.; Frencel, I.; Robinson, J. B. Can. J. Chem. 1977, 55, 4180.
9. For the preparation of Cyclopentylamino alcohol, see: (a) Barnard, H. Can. J. Chem. 1958, 36, 1252; (b) Overman, L. E.; Sugai, S. J. Org. Chem. 1985, 50, 4154; (c) Barr, A.; Frencel, I.; Robinson, J. B. Can. J. Chem. 1977, 55, 4180.
10. For the preparation of Cyclopentylamino alcohol, see: (a) Barnard, H. Can. J. Chem. 1958, 36, 1252; (b) Overman, L. E.; Sugai, S. J. Org. Chem. 1985, 50, 4154; (c) Barr, A.; Frencel, I.; Robinson, J. B. Can. J. Chem. 1977, 55, 4180.
11. Nitrosation as well as nitration of 2a were both poor yielding reactions leading to a mixture of products. After partial purification, when these compounds were reacted with 6, they led to a complex mixture of products. For these reasons the methoxy group was deemed less desirable than the thiomethyl group, and hence it is not described in this manuscript.
12. Gala D., Puar M.S., Czarniecki M., Das P.R., Kugelman M., Kaminiski J. Tetrahedron Lett. 41:2000;5025.
13. 5COCl. 50% Water Wet 5% Pd/C used for hydrogenation reaction was the source of water in reaction medium.
14. 3 was preformed to prevent hydrolysis of the products (Ref. 7).