A solid phase approach to substituted pyrimidines and their conversion into condensed heterocycles for potential use in combinatorial chemistry

Combinatorial Chemistry and High Throughput Screening

Volumn 2, Issue 1, 1999, Pages 33-37

  Srivastava, Sanjay K ^b   Haq, W ^a   Chauhan, P M S ^b  

^a Medicinal and Process Chemistry Division   (India)

^b CENTRAL DRUG RESEARCH INSTITUTE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

HETEROCYCLIC COMPOUND; PYRIMIDINE DERIVATIVE; RESIN;

ARTICLE; CHEMICAL REACTION; CHEMISTRY; CYCLIZATION; POLYMERIZATION; PRIORITY JOURNAL; SOLID; SYNTHESIS;

HETEROCYCLIC COMPOUNDS; INDICATORS AND REAGENTS; PYRIMIDINES;

STAPHYLOCOCCUS PHAGE 3A;

EID: 0032980932     PISSN: 13862073     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (20)

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5. Srivastava, S.K., Chauhan, P.M.S.; Bhaduri, A.P.; Agarwal, S.K.; Singh, S.N.; Fatma, N.; Chatterjee, R.K.; Bose, C.; Srivastava, V.M.L. Bioorg. & Med. Chem. Lett., 1996, 6, 2623.
6. Srivastava, S., Tewari, S., Srivastava, S.K.; Puri, S.K., Chauhan, P.M.S.; Bhaduri, A.P.; Pandey, V.C. Bioorg. & Med. Chem. Lett., 1997, 7, 2741.
7. In "Comprehensive Heterocyclic Chemistry, Eds. A.R. Katritzky and C.W. Rees, Pergamon Press, New York, 1984, 1, pp. 43.
8. In "Comprehensive Heterocylic Chemistry" Eds. A.R. Katritzky and G.W. Rees. Pergamon Press, Oxford, 1984, 3, pp. 57.
9. Wright, G.E.; Gambino, J.J. J. Med. Chem., 1984, 27, 181.
10. Ban, M.; Taguchi, H.; Katsushima, T.; Aoki, S.; Watanabe, A. Bioorg. & Med. Chem. 1998, 6, 1057.
11. Jalander, L.F.; Longquist, J.E., Heterocycles, 1998, 48(4), 743.
12. 2 (100 ml) and MeOH (100 ml). The polymer-bound thiouronium salt was then dried at 60°C under high vaccum for 24 hr.
13. 2EtN (3 ml) were added. After stirring at room temperature for 60 h, the mixture was filtered and washed successively with DMF (50 ml), THF (50 ml) and MeOH (50 ml), the resulting resin was dried at 50°C under high vaccum for 10 hr.
14. 4 (5 ml), as in scheme 2, at room temperature. The mixture was then filtered and washed successively with water (25 ml) and methanol (25 ml). The resulting resin was then dried at 65°C under high vaccum for 15 hr.
15. The respective resin (3 mmol) as in scheme 2 and 3 was hydrogenated using Rany Ni in EtOH (20 ml) as solvent for 12 hr and then filtered in hot condition. Filtrate was concentrated in vacuo to provide the compound.
16. A mixture of resin (3 mmol) and oxone (500 mg) in dioxane/water (4:1, 25 ml) was stirred at room temperature for 2 h. It was then filtered and washed successively by dioxane (20 ml), DMF (20 ml) and MeOH (20 ml). The resulting resin was then dried at 75°C under high vaccum for 10 hr.
17. A mixture of resin (3 mmol), amine (5 mmol) in DMF (30 ml) was stirred at 60°C for 4-12 hr. It was then filtered and filtrate was then concentrated in vacuo to afford a residue which was then washed by hexane to provide the product.
18. 4 and then combined extract was concentrated to afford the compound 11.
19. 2 (50 ml) and MeOH (50 ml). The resin was dried at 65°C under high vaccum.
20. 2 (50 ml) and MeOH (50 ml) and was dried at 65°C under high vaccum.