Diaminopyrimidine and diaminopyridine 5-HT7 ligands

Bioorganic and Medicinal Chemistry Letters

Volumn 14, Issue 16, 2004, Pages 4249-4252

  Denhart, Derek J ^a   Purandare, Ashok V ^a   Catt, John D ^a   Dalton King, H ^a   Gao, Aiming ^a   Deskus, Jeffrey A ^a   Poss, Michael A ^a   Stark, Arlene D ^a   Torrente, John R ^a   Johnson, Graham ^a   Mattson, Ronald J ^a  

^a BRISTOL MYERS SQUIBB   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PYRIDINE DERIVATIVE; SEROTONIN 7 RECEPTOR;

ARTICLE; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; LIGAND BINDING; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

LIGANDS; PYRIDINES; PYRIMIDINES; RECEPTORS, SEROTONIN;

EID: 3142736443     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2004.06.007     Document Type: Article

References (11)

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3. Mullins U.L., Gianutsos G., Eison A.S. Neuropsychopharmacology. 21:1999;352-367
4. Terron J.A., Falcon-Neri A. Brit. J. Pharmacol. 127:1999;609-616
5. Pouzet B., Didriksen M., Arnt J. Pharm. Biochem. Behav. 71:2002;655-665
6. Mattson, R. J.; Denhart, D. J.; Catt, J. D.; Dee, M. F.; Deskus, J. A.; Ditta, J. L.; Epperson, J.; King, H. D.; Gao, A.; Poss, M. A.; Purandare, A.; Tortolani, D.; Zhao, Y.; Yang, H.; Yeola, S.; Palmer, J.; Torrente, J.; Stark, A.; Johnson, G. Bioorg. Med. Chem. Lett., 2004, 14, in press. doi:10.1016/j.bmcl.2004.06.008.
7. Procedure for synthesis of 11: A mixture of 4, 6-dichloro-pyrimidine (14.9 g, 0.10 mol), (S)-(-)-α-methylbenzylamine (13.3 g, 0.11 mol), and diisopropylethylamine (15.5 g, 0.12 mol) in acetonitrile (100 mL) were heated to reflux for 4 h. The reaction was cooled, then partitioned between ether (500 mL) and water (250 mL). The organic layer was separated, dried over sodium sulfate, and concentrated in vacuo. Purification by flash chromatography on silica gel with hexane/ethyl acetate (3:1) yielded pure (S)-6-chloro-N-(1- phenylethyl)pyrimidin-4-amine (18.6 g, 80%).
8. i values are determined using nonlinear regression by Exel-fit
9. d concentration. Each experiment was carried out in duplicate. Standard errors were typically ±20% of the mean value
10. Wagaw S., Buchwald S.L. J. Org. Chem. 61:1996;7240-7241
11. 1H NMR spectra.