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Ethyl 2-(n-Butylamino)-7-hydroxy-5-methylpyrazolo[1,5-a]pyrimidine-3-carboxylate.doc

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Ethyl 2-(n-Butylamino)-7-hydroxy-5-methylpyrazolo[1,5-a]pyrimidine-3-carboxylate

Molecules 2000, 5, M143 Ethyl 2-(n-Butylamino)-7-hydroxy-5-methylpyrazolo[1,5-a]pyrimidine-3-carboxylate Lajos Kovács1,* and Péter Forgó2 1Department of Medicinal Chemistry and 2Department of Organic Chemistry, University of Szeged, Dóm tér 8., H-6720 Szeged, Hungary. 1Phone: +36 62 54 51 45, 2Phone: +36 62 54 36 78, 1Fax: +36 62 42 52 62, 2Fax: +36 62 42 57 68, 1E-mail: kovacs@ovrisc.mdche.u-szeged.hu, 2E-mail: pforgo@sol.chem.u- szeged.hu,1URL:www.mdche.u-szeged.hu/staff/kovacs.htm2URL:www.jate.u-szeged.hu/orgchem Received: 20 January 2000 / Accepted: 8 February 2000 / Published: 23 February 2000 Ethyl 2-cyano-3,3-bis(methylthio)acrylate 1 [1] (3.255 g; 15.0 mmol) was dissolved in anhydrous ethanol (100 mL), n-butylamine (1.100 g; 15.0 mmol) was added and the solution was heated to reflux for 2 h in a flask equipped with a gas outlet to remove the evolving methanethiol (hood). The reaction mixture was evaporated and the product (2, 3.59 g, 99 %) was obtained as a yellowish oil. Tlc (light petroleum : ethyl acetate 8 : 2): single spot (Rf 0.67). 1H NMR (200 MHz, CDCl3): 0.97 (t, J 7.0 Hz, 3 H, CH3CH2O); 1.29-1.46 (m, 4 H, 2 x CH2); 1.63 (t, J 7.4 Hz, 3 H, CH3); 2.70 (s, 3 H, SCH3); 3.53 (m, 2 H, CH2); 4.23 (q, J 7.0 Hz, 2 H, CH3CH2O); 10.08 (br s, 1 H, NH). This intermediate (ethyl 2-cyano-3-n-butylamino-3-methylthioacrylate, 2) was again dissolved in anhydrous ethanol (100 mL), hydrazine hydrate (0.74 mL; 15.0 mmol) was added and the solution was heated to reflux for 3 h (hood). The reaction mixture was evaporated and the resulting oil was triturated with hexane. After the ensuing crystallization, filtration, and washing with hexane, the product (ethyl 5-amino-3-n-butylamino-1H-pyrazole- 4-carboxylate, 3) was obtained (3.235 g; 97 %) as white crystals, mp. 103-104 °C. Tlc (CHCl3 : MeOH 9 : 1): single spot (Rf 0.42). Compound 3 (3.215 g, 14.21 mmol) was dissolved in glacial acetic acid (5 mL), a solution of ethyl acetoacetate (1.811 mL, 14.21 mmol) in g