One-pot syntheses of 6-mercaptopurines (6MP) from 4,5-diamino-6-chloro- pyrimidines

Tetrahedron Letters

Volumn 45, Issue 11, 2004, Pages 2321-2322

  Tandel, Sagun ^a   Bliznets, Igor ^a   Ebinger, Katalin ^a   Ma, You An ^a   Bhumralkar, Dilip ^b   Thiruvazhi, Mohan ^a  

^a ChemBridge Research Laboratories   (United States)

^b PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United States)

Author keywords

4,5 Diamino 6 chloro pyrimidines; H2S; One pot synthesis; Thiopurines

Indexed keywords

6 MERCAPTOPURINE DERIVATIVE; ALDEHYDE DERIVATIVE; PYRIMIDINE DERIVATIVE; SULFUR DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY;

EID: 1242270593     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.01.105     Document Type: Article

References (10)

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5. Chun B.K., Olgen S., Hong J.H., Newton M.G., Chu C.K. J. Org. Chem. 65:2000;685-693.
6. Sulfur has been used for the synthesis of 2-arylimidazo[4,5-b]- and 2-arylimidazo[4,5-c]-pyridines from o-/m-diaminopyridines and aromatic aldehydes. See: Yutilov Y.M., Shcherbina L.I. Chem. Heterocycl. Compd. 23(5):1987;529-535.
7. +].
8. Dubey P.K., Ratnam C.V. Proc. Indian Acad. Sci. 85A:1977;204.
9. When aniline was treated with benzaldehyde and sulfur in hot DMF, N-phenylbenzenecarbothioamide was obtained in high yields. For similar published results, see: Pelova R., Kozhukharova A. Nauchni, Trudove Plovdivski Universitet Paisii Khilendarski. 20(3, Khim):1982;79-90.
10. 2S is from the observation that when phenylenene diamine, m-hydroxybenzaldehyde and 6-chloro-9-cyclopentyl-9H-purine were subjected to the reaction conditions, the expected 3-(1H-benzimidazol-2-yl)phenol and 9-cyclopentyl-9H-purine-6-thiol were obtained. However, no mercapto product was obtained in the absence of the diamine and benzaldehyde.